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[ CAS No. 1010120-55-4 ] {[proInfo.proName]}

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Chemical Structure| 1010120-55-4
Chemical Structure| 1010120-55-4
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Quality Control of [ 1010120-55-4 ]

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Product Details of [ 1010120-55-4 ]

CAS No. :1010120-55-4 MDL No. :MFCD11655928
Formula : C6H5BrN4 Boiling Point : -
Linear Structure Formula :- InChI Key :TVGFHUIJNZRKFW-UHFFFAOYSA-N
M.W : 213.04 Pubchem ID :25215939
Synonyms :

Calculated chemistry of [ 1010120-55-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.09
TPSA : 56.21 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.42
Log Po/w (WLOGP) : 1.08
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 1.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.465 mg/ml ; 0.00218 mol/l
Class : Soluble
Log S (Ali) : -2.21
Solubility : 1.33 mg/ml ; 0.00624 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.21
Solubility : 1.3 mg/ml ; 0.00612 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 1010120-55-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1010120-55-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1010120-55-4 ]

[ 1010120-55-4 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 288-13-1 ]
  • [ 1010120-55-4 ]
  • [ 1124382-69-9 ]
YieldReaction ConditionsOperation in experiment
65% With potassium hydroxide; at 110℃; Intermediate A12 : 5-flH-pyrazol-l-yl)[l,2,41triazolo[l,5-alpyridin-2-amine; Intermediate A125-bromo[l,2,4]triazolo[l,5-a]pyridin-2-amine ((A3); 1,06 g; 5.0 mmol; 1.0 eq.), pyrazole (3.40 g; 50.0 mmol; 10 eq.) and potassium hydroxide (842 mg; 15.0 mmol; 3.0 eq.) were melted and stirred overnight at 110 0C. After this time, reaction mixture was cooled to rt poured into water and extracted with Et2O. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the title compound as a white solid (650 mg, 65%). HPLC, Rt: 1.22 min. (purity 96.6%). LC/MS, M+(ESI): 201.0.
  • 3
  • [ 1010120-55-4 ]
  • [ 98-88-4 ]
  • [ 1124382-75-7 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; In dichloromethane; for 4h;Heating / reflux; Intermediate Bl : N-f5-bromo[l,2,41triazolo[l,5-alpyridin-2-yl)benzamide; Intermediate BlBenzoyl chloride (4.40 g; 31.4 mmol; 2.0 eq.) was added to a suspension of 5- bromo[l,2,4]triazolo[l,5-a]pyridin-2-amine ((A3), 3.34 g; 15.7 mmol; 1.0 eq.) in pyridine (2.53 mL; 31.4 mmol; 2.0 eq.) and DCM (60 mL). The reaction mixture was then heated at <n="69"/>reflux for 4 hours, after which it was cooled down to rt. Diethyl ether was added to the reaction mixture and the solid which precipitated was filtered off. The precipitate was resuspended in an aqueous mixture (pH 4/5), filtered and dried under vacuum to give the title compound as a white powder (4.97 g, quant, yield). HPLC, Rt: 2.40 min. (purity 93.4%), LC/MS, M+(ESI): 317.1, M (ESI): 315.1.
  • 4
  • [ 1010120-55-4 ]
  • [ 63503-60-6 ]
  • [ 1111106-76-3 ]
YieldReaction ConditionsOperation in experiment
61% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); at 150℃; for 1h;Microwave irradiation; A suspension of 5-bromo[l,2,4]triazolo[l,5-alpha]pyridin-2-amine (5.1 g, 24 mmol, 1 equiv), 3-chlorophenylboronic acid (3.8 g, 24 mmol, 1.0 equiv), cesium carbonate (9.4 g, 29 mmol, 1.2 equiv), tetrakistriphenylphosphine palladium (2.7 g, 2.4 mmol, 0.1 equiv) was heated to 150 C for 1 h under <n="96"/>microwave irradiation. The reaction mixture was diluted with ethyl acetate and filtered through Celite. The filtrate was washed with saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (30% ethyl acetate in petroleum ether) provided product as a solid (3.5 g, 61%). LCMS (ESI) m/z: 244.9.
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 5h;Reflux; Compound 14Compound 13 (750 mg, 3.5 mmol) was dissolved in toluene/ethanol (1 :1, 20 ml), to which was added 2M aqueous Na2CO3 (3.5 ml) and 3- chlorophenylboronicacid (1.1 g, 7.0 mmol). Pd (PPh3) 4 (202 mg) was added last, the mixture was flushed with nitrogen and refluxed for 5 hours in a sealed tube. The reaction mixture was allowed to cool.The reaction solvent was removed and the residue was purified on silica gel (ethylacetate : hexanes 50%) to give 514mg of compound 14 as white solid. LC-MS (ESI, positive): 247 [M+H]+.
  • 5
  • [ 1010120-59-8 ]
  • [ 1010120-55-4 ]
YieldReaction ConditionsOperation in experiment
79.5% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 70℃; for 3.5h; A solution was ethyl [(6-methylpyridin-2-yl)carbamothioyl]carbamate (43.7 g, 0.144 mmol, 1 equiv), hydroxylamine hydrochloride (51.3 g, 0.738 mmol, 5.13 equiv), and diisopropylethylamine (75.2 mL, 0.432 mmol, 3.00 equiv) in 1:1 methanol / ethanol (500 mL) was heated to 70 0C for 3.5 h. The reaction mixture was cooled to 24 C, and the resulting solids were filtered.The solids were rinsed with cold water (2 x 100 mL) and dried in vacuo (~1 mm Hg) to afford product as a white solid (24.4 g, 79.5%). 1H NMR (400 MHz, OMSO-d6), delta: 7.32-7.38 (m, 2 H), 7.21 (m, 1 H), 6.23 (br s, 2 H).
78% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20℃; for 4h;Reflux; Step (ii)To a suspension of hydroxylamine hydrochloride (85.5g, 1230mmol) in EtOH/MeOH (1 : 1, 400mL) was added DIPEA (129mL, 738mmol) and the mixture was stirred at rt (20C) for lh. l-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (74.7g, 246mmol) was then added and the mixture slowly heated to reflux (Note: bleach trap required to quench H2S evolved). After 3h at reflux the mixture was allowed to cool overnight. The resulting precipitate was removed by filtration and washed thoroughly with water followed by diethylether and air-dried to afford the desired compound as a white solid (41g, 78%). LCMS (method A), (M+H+) 213/215, RT = 0.70min.
74% With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20 - 60℃; for 20h;Product distribution / selectivity; To a stirred suspension of hydroxylamine hydrochloride (20.0 g, 288 mmol) and N,N-diisopropylethylamine (30.0 mL, 172 mmol) in a mixture of methanol (80 mL) and ethanol (80 mL) was added N-(3-bromo-2-pyridinyl)-N'-carboethoxy-thiourea. The mixture was stirred for 2 hours at room temperature then heated to 600C for 18 hours. The suspension was cooled to room temperature, filtered and rinsed with methanol, water then methanol. The recovered off-white solid was consistent for 5-bromo-[l,2,4]triazolo[l,5- a]pyridin-2-ylamine (9.04 g, 74%). 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 7.36 (m, 2H), 7.22 (d, J= 7.5 Hz, IH), 6.27 (br s, 2H) MS = 213, 215 (MH)+.
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20 - 60℃; for 5h; Compound 13To a stirred suspension of hydroxylamine hydrochloride (959.1 g, 13.8 mmol) and DIPEA (1.2 g, 9.2 mmol) in methanol/ethanol (1 : 1 , 50 ml) was added compound 12 (1.4 g, 4.6 mmol) as solid. The mixture was stirred at room temperature for 2 hours, followed by 3hours at 600C. The reaction mixture wasallowed to cool, diluted with CH2Cl2, which was then washed with water (2chi80 ml), the organic phase was evaporated and the residue was chromatographed in MeOH/ CH2Cl2 (8% -10%) to afford 750 mg of compound 13 as a white solid. LC-MS (ESI, positive): 215 [M+H]+.
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20℃;Reflux; To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1:1,900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (2O0C) for 1 h. l-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) may then be added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3 h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product may be collected by evaporation in vacuo of the filtrate, addition of H2O (250 mL) and filtration. The combined solids are washed successively with H2O (250 mL), EtOH/MeOH (1 :1, 250 mL) and Et2O (250 mL) then dried in vacuo to afford (3) as a solid. No further purification is required. 1H (400 MHz, DMSO-d6) delta: 7.43-7.34 (2H, m, 2 Hz aromatic-H), 7.24 (IH, dd, J 6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, b, NH2); m/z 213/215 (1 :1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20℃;Reflux; To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1:1, 900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (20 C.) for 1 h. 1-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) may then be added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3 h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product may be collected by evaporation in vacuo of the filtrate, addition of H2O (250 mL) and filtration. The combined solids are washed successively with H2O (250 mL), EtOH/MeOH (1:1, 250 mL) and Et2O (250 mL) then dried in vacuo to afford the triazolopyridine derivative (3) as a solid. The compound may be used as such for the next step without any purification. 1H (400 MHz, DMSO-d6) delta 7.43-7.34 (2H, m, 2* aromatic-H), 7.24 (1H, dd, J 6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1:1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; water; for 3h;Reflux; 1.1.2 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (3) To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1:1, 900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (20 C.) for 1 h. 1-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) is then added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3 h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product is collected by evaporation in vacuo of the filtrate, addition of H2O (250 mL) and filtration. The combined solids are washed successively with H2O (250 mL), EtOH/MeOH (1:1, 250 mL) and Et2O (250 mL) then dried in vacuo to afford the triazolopyridine derivative (3) as a solid. The compound may be used as such for the next step without any purification. 1H (400 MHz, DMSO-d6) delta 7.43-7.34 (2H, m, 2*aromatic-H), 7.24 (1H, dd, J 6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1:1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20℃; for 3h;Reflux; To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH(1:1, 900 mL) was added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture wasstirred at room temp. (20 oq for 1 h. 1-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g,0.293 mol) was then added and the mixture slowly heated to reflux (Note: bleach scrubber wasrequired to quench H2S evolved). After 3 h at reflux, the mixture was allowed to cool and filtered tocollect the precipitated solid. Further product was collected by evaporation in vacuo of the filtrate,addition of H20 (250 mL) and filtration. The combined solids were washed successively with H20 (250 mL), EtOH/MeOH (1:1, 250 mL) and Et20 (250 mL) then dried in vacuo to afford thetriazolopyridine derivative (3) as a solid. The compound was used as such in the next step without anypurification.[00159] 1H ( 400 MHz, DMSO-d6) 8 7.43-7.34 (2H, m, 2 x aromatic-H), 7.24 (lH, dd, J 6.8 and 1.8Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1:1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; for 3h;Reflux; 1.1.2.2. Step ii): 5-Bromo-[1,2,4]triazolo[1,5-a]kyridin-2-ylamine To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1:1, 900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (20 C.) for 1 h. 1-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) is then added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product is collected by evaporation in vacuo of the filtrate, addition of H2O (250 mL) and filtration. The combined solids are washed successively with H2O (250 mL), EtOH/MeOH (1:1, 250 mL) and Et2O (250 mL) then dried in vacuo to afford the triazolopyridine derivative (3) as a solid. The compound may be used as such for the next step without any purification. 1H (400 MHz, DMSO-d6) delta 7.43-7.34 (2H, m, 2×aromatic-H), 7.24 (1H, dd, J6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1:1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; at 20℃;Reflux; Step ii : 5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1:1, 900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (20 C.) for 1 h. 1-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) is then added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3 h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product is collected by evaporation in vacuo of the filtrate, addition of H2O (250 mL) and filtration. The combined solids are washed successively with H2O (250 mL), EtOH/MeOH (1:1, 250 mL) and Et2O (250 mL) then dried in vacuo to afford the triazolopyridine derivative (3) as a solid. The compound may be used as such for the next step without any purification. 1H (400 MHz, DMSO-d6) delta 7.43-7.34 (2H, m, 2* aromatic-H), 7.24 (1H, dd, J 6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1:1, M+H+, 100%).
With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; for 3h;Reflux; [0165] To a suspension of hydroxylamine hydrochloride (101.8 g, 1.465 mol) in EtOH/MeOH (1 : 1, 900 mL) is added N,N-diisopropylethylamine (145.3 mL, 0.879 mol) and the mixture is stirred at room temp. (20 C) for 1 h. l-(6-Bromo-pyridin-2-yl)-3-carboethoxy-thiourea (2) (89.0 g, 0.293 mol) is then added and the mixture slowly heated to reflux (Note: bleach scrubber is required to quench H2S evolved). After 3 h at reflux, the mixture is allowed to cool and filtered to collect the precipitated solid. Further product is collected by evaporation in vacuo of the filtrate, addition of H20 (250 mL) and filtration. The combined solids are washed successively with H20 (250 mL), EtOH/MeOH (1 : 1, 250 mL) and Et20 (250 mL) then dried in vacuo to afford the triazolopyridine derivative (3) as a solid. The compound may be used as such for the next step without any purification. [0166] lH (400 MHz, DMSO-dg) delta 7.43-7.34 (2H, m, 2 x aromatic-H), 7.24 (1H, dd, J 6.8 and 1.8 Hz, aromatic-H), 6.30 (2H, br, NH2); m/z 213/215 (1 : 1, M+H+, 100%).
6 g With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In ethanol; at 20℃; for 4h;Reflux; Step 2, 5-bromo-[1,2,4]triazolo[1,5a]pyridin-2-ylamine 10.0g of hydroxylamine hydrochloride was dissolved in 100 ml of ethanol, 14.5 ml of N,N-diisopropylethylamine was added, and the reaction was stirred at room temperature for 1 hour. 9 g of the product of step 1 was then added, and the mixture was heated under reflux. After 3 hours, the mixture was cooled and solid was precipitated. The solid was filtered, washed, and air-dried to afford 6 g of the desired product.

  • 6
  • [ 1010120-55-4 ]
  • [ 75-36-5 ]
  • [ 1206101-26-9 ]
YieldReaction ConditionsOperation in experiment
N-(5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-acetamide To a solution of the 5-bromo-2-amino-triazolopyridine (1 eq.) in dry CH3CN at 5 C. is added Et3N (2.5 eq.) followed by acetyl chloride (2.5 eq.). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material is consumed. If required, further Et3N (1 eq.) and acid chloride (1 eq.) are added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution and stirred at ambient temp. (for 16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by addition of water and extraction with ethyl acetate. The organic phase is then dried over MgSO4, evaporated in vacuo. The compound is used without further purification.
  • 7
  • [ 1010120-55-4 ]
  • [ 4023-34-1 ]
  • [ 1142943-96-1 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine; In 1,2-dichloro-ethane; at 20℃; <strong>[1010120-55-4]5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine</strong> (10 g, 50 mmol) and triethylamine (10 g, 100 mmol) in dichloroethane (200 mL) Cyclopropionyl chloride (5.7 g, 55 mmol) was added and stirred at room temperature overnight. After the reaction mixture was diluted, it was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate and evaporated. Purification by silica gel column chromatography gave white solid (10 g, 76%)
58% Step (Hi)5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-amine (10.7g, 50mmol) was suspended in acetonitrile (200mL) and DIPEA (9.6mL, 55mmol). Cyclopropanecarbonyl chloride (5.0mL, 55mmol) and 4-(Dimethylamino)pyridine (287mg, 2.35mmol) were added in one portion and the suspension heated at 80C for 18h. After this time the solvents were removed in vacuo and the resulting solid was stirred in ammonia/methanol (2M) for 2h at rt. The solvents were removed in vacuo and the resulting solid was triturated, filtered and washed with diethyl ether (3 x lOOmL) to afford the desired compound as a white solid (8.12g, 58% ). LCMS (method A), (M+H+) 281/283, RT = 0.78min.
56.64% To <strong>[1010120-55-4]5-bromo-[1,2,4] triazolo[1,5-a]pyridin-2-amine</strong>(15.00 g, 70.41 mmol) and triethylamine(21.4 g, 211.2 mmol), dissolved in acetonitrile(150 mL) was added dropwise cyclopropanecarboxylic acid chloride(8.8 g, 84.5 mmol) at 0C. After adding, the mixture was warmed to room temperature for the reaction for 16 hours. After TLC showed that the reaction was completed through monitoring, the reaction mixture was distilled under reduced pressure. The resulting residue was dissolved in an alcoholic solution of methylamine(150 mL), heated to 80C for the reaction for 1 hour, cooled, distilled under reduced pressure. The resulting residue was dissolved in mixed solution of water(100 mL) and ethyl acetate(200 mL), and the layers were separated and extracted. The combined organic phase was dried with anhydrous sodium sulfate and filtered, and the filtrate was distilled under reduced pressure. The resulting crude product was purified through silica gel column chromatography (eluting with ethyl acetate/petroleum ether =0?70%) to give N-(5-bromo-[1,2,4]triazolo[1,5-a] pyridin-2-yl)cyclopropyl carboxamide (7.2 g, 56.64% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta = 11.20 (br. s., 1 H), 7.68 - 7.73 (m, 1 H), 7.52 - 7.58 (m, 1 H), 7.46 - 7.51 (m, 1 H), 1.96 - 2.09 (m, 1 H), 0.82 (d, J=6.28 Hz, 4 H). MS (ESI) Calcd. for C10H9 BrN4O [M + H]+ 282, Found 282.
To a solution of the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 50C is added Et3N (11.6 mL, 83.3 mmol) followed by the appropriate acid chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and acid chloride (33.3 mmol) may be added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp, (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids may be collected by filtration, washed with H2O (2x50 rnL), acetone (50 rnL) and Et2O (50 rnL), then dried in vacuo to give the required intermediate (4). In some cases column chromatography (petrol/EtOAc) may be required to obtain pure compounds.
To a solution of the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 5 C. is added Et3N (11.6 mL, 83.3 mmol) followed by the appropriate acid chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and the acid chloride (33.3 mmol) may be added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp. (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids may be collected by filtration, washed with H2O (2×50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the required acyl intermediate (4). In some cases column chromatography (petrol/EtOAc) may be required to obtain pure compounds.
1.1.3 General Procedure for Mono-Acylation to Afford Intermediate (4) To a solution of the 2-amino-triazolopyridine (3) (7.10 g, 33.3 mmol) in dry CH3CN (150 mL) at 5 C. is added Et3N (11.6 mL, 83.3 mmol) followed by cyclopropanecarbonyl chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material (3) is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and cyclopropanecarbonyl chloride (33.3 mmol) is added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp. (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids are collected by filtration, washed with H2O (2*50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the required bromo intermediate (4).
With triethylamine; In acetonitrile; at 5 - 20℃; Step iii : Cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide To a solution of the 2-amino-triazolopyridine obtained in the previous step (7.10 g, 33.3 mmol) in dry MeCN (150 mL) at 5 C. is added Et3N (11.6 mL, 83.3 mmol) followed by cyclopropanecarbonyl chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and cyclopropanecarbonyl chloride (33.3 mmol) is added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp. (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids are collected by filtration, washed with H2O (2*50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the desired compound.
Step iii : Cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide To a solution of the 2-amino-triazolopyridine obtained in the previous step (7.10 g, 33.3 mmol) in dry MeCN (150 mL) at 5 C. is added Et3N (11.6 mL, 83.3 mmol) followed by cyclopropanecarbonyl chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and cyclopropanecarbonyl chloride (33.3 mmol) is added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp. (for 1-16 h) to hydrolyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et2O (50 mL). The solids are collected by filtration, washed with H2O (2*50 mL), acetone (50 mL) and Et2O (50 mL), then dried in vacuo to give the desired compound.
With triethylamine; In acetonitrile; at 5 - 20℃; [0167] To a solution of the 2-amino-triazolopyridine obtained in the previous step (7.10 g, 33.3 mmol) in dry MeCN (150 mL) at 5C is added Et3N (11.6 mL, 83.3 mmol) followed by cyclopropanecarbonyl chloride (83.3 mmol). The reaction mixture is then allowed to warm to ambient temperature and stirred until all starting material is consumed. If required, further Et3N (4.64 mL, 33.3 mmol) and cyclopropanecarbonyl chloride (33.3 mmol) is added to ensure complete reaction. Following solvent evaporation in vacuo the resultant residue is treated with 7 N methanolic ammonia solution (50 mL) and stirred at ambient temp, (for 1 h-16 h) to hydro lyse any bis-acylated product. Product isolation is made by removal of volatiles in vacuo followed by trituration with Et20 (50 mL). The solids are collected by filtration, washed with H20 (2x50 mL), acetone (50 mL) and Et20 (50 mL), then dried in vacuo to give the desired compound
4.5 g With pyridine; at -50℃; for 0.166667h; Add 50mL pyridine to the reaction flask,Cyclopropane chloride (2.9 g, 28 mmol) was added dropwise to the reaction flask at -50C.Stir for 10 minutes,5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (5 g, 23 mmol) was then added to the reaction flaskin,The reaction was stirred overnight at room temperature.After the reaction is completed,Add 100 mL of petroleum ether to the reaction solution.FilteringFilter cake washed twice with petroleum ether, Each time 100mL,Then wash once with 100mL of waterTo get the title product,Earth gray solid 4.5g
4 g With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 5h; 100 ml of 6 dichloromethane and 9 g of 12 diisopropylethylamine were added to 5 g of the product of Step 2. The mixture was cooled to 0 C in an ice bath. 6.1 g of 15 cyclopropanecarbonyl chloride was added dropwise. The mixture became clear after 1 hour of reaction. After the reaction was continued for 4 hours, the reaction system was concentrated to dryness to give an oily 16 solid. Then, a mixed solution of 7 ml of ammonia water and 43 ml of methanol was added to the oily solid under cooling in an ice salt bath, and stirred for about 3 hours. The system became a brown turbid liquid. After filtration by suction, the solid was washed with water and dried to obtain 4 g of the target.

  • 8
  • [ 1010120-55-4 ]
  • [ 5720-07-0 ]
  • [ 1142943-95-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 90 - 140℃;Microwave irradiation; An appropriate Ar substituted boronic acid derivative (2eq.) is added to a solution of 2-amino-8- bromo-triazolopyridine (Commercially available, BiofocusDPI) in dioxan/water (5: 1). K2CO3 (2 eq.) and PdCl2dppf (5%) are added to the mixture. The resulting mixture is heated in a microwave oven at 1400C for 15-45 min or heated in an oil bath at 900C for 4 to 16 h until the reaction goes to completion (monitored by LCMS). Water is added and the mixture is extracted with ethyl acetate. The organic layers are combined, dried over anhyd. MgSO4 and evaporated in vacuo to yield the crude product. The crude product is then purified by flash chromatography to give the corresponding 2-amino-5-Ar-triazolopyridine derivative (2).
  • 9
  • [ 636-98-6 ]
  • [ 1010120-55-4 ]
  • [ 1206195-33-6 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In toluene;Sonographic reaction; Inert atmosphere; A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), BINAP (0.1 eq), l-Iodo-4-nitro-benzene (1.5 eq) and 1,4-dioxan was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1200C or in a flasked equipped with a cooling system for 16 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The crude product was then purified by preparative HPLC to give the corresponding (5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-yl)-(4-nitro-phenyl)-amine.
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In 1,4-dioxane;Sonographic reaction; Inert atmosphere; A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), BINAP (0.1 eq), 1 -Iodo-4-nitro-benzene (1.5 eq) and 1,4-dioxan was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1200C or in a flasked equipped with a cooling system for 16 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The crude product was then purified by preparative HPLC to give the corresponding (5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-yl)-(4-nitro-phenyl)-amine
  • 10
  • [ 591-50-4 ]
  • [ 1010120-55-4 ]
  • [ 1206195-26-7 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;palladium diacetate; In 1,4-dioxane;Sonographic reaction; Inert atmosphere; A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), Xantphos (0.1 eq.), Iodobenzene (1.5 eq) and 1,4-dioxane were sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1000C or in a flasked equipped with a cooling system for 5 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The crude product was purified by flash chromatography.
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;palladium diacetate; In 1,4-dioxane;Sonographic reaction; A mixture of 5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), Xantphos (0.1 eq.), iodobenzene (1.5 eq) and 1,4-dioxane is sonicated for 5 minutes under nitrogen. Afterwards, the reaction is left in a sealed tube at 1000C or in a flask equipped with a cooling system for 5 hrs. The crude mixture is extracted with ethyl acetate and the extracts are combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent is removed under high vacuum to yield the crude product. The crude product may be purified by flash chromatography.
  • 11
  • [ 1010120-55-4 ]
  • [ 51934-41-9 ]
  • [ 1206195-39-2 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;palladium diacetate; In 1,4-dioxane;Sonographic reaction; Inert atmosphere; A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), BINAP (0.1 eq), 4-Iodo-benzoic acid ethyl ester (1.5 eq) and 1,4-dioxane was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1200C or in a flasked equipped with a cooling system for 16 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The product was used in the next step without futher purification.
  • 12
  • [ 1010120-55-4 ]
  • [ 619-44-3 ]
  • [ 1206195-27-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;palladium diacetate; In 1,4-dioxane;Sonographic reaction; Inert atmosphere; A mixture of 5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), Xantphos (0.1 eq.), 4-Iodo-benzoic acid methyl ester (1.5 eq) and 1,4-dioxane was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1000C or in a flasked equipped with a cooling system for 5 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The crude product was purified by flash chromatography.
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;palladium diacetate; In 1,4-dioxane;Sonographic reaction; A mixture of 5-Bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine (1 eq), Cs2CO3 (5eq), Pd(OAc)2 (0.1 eq), Xantphos (0.1 eq.), 4-Iodo-benzoic acid methyl ester (1.5 eq) and 1,4-dioxane was sonicated for 5 minutes under nitrogen. Afterwards, the reaction was left in a sealed tube at 1000C or in a flasked equipped with a cooling system for 5 hrs. The crude mixture was extracted with ethyl acetate and the extracts were combined, washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed under high vacuum to yield the crude product. The crude product was purified by flash chromatography.
  • 13
  • [ 389621-83-4 ]
  • [ 1010120-55-4 ]
  • C18H19N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; An appropriate Ar substituted boronic acid derivative (2eq.) is added to a solution of 2-amino-8-bromo-triazolopyridine (Commercially available, BiofocusDPI) in dioxan/water (5:1). K2CO3 (2 eq.) and PdC^dppf (5%) are added to the mixture. The resulting mixture is heated in a microwave oven at 1400C for 15-45 min or heated in an oil bath at 900C for 4 to 16 h until the reaction goes to completion (monitored by LCMS). Water is added and the mixture is extracted with ethyl acetate. The organic layers are combined, dried over anhyd. MgSO4 and evaporated in vacuo to yield the crude product. The crude product is then purified by flash chromatography to give the corresponding 2-amino-5-Ar-triazolopyridine derivative (2).
  • 14
  • [ 1010120-55-4 ]
  • [ 4334-88-7 ]
  • [ 1206594-04-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 140℃; under 7757.43 Torr; for 1h;Microwave irradiation; 4-Ethoxycarbonyl-phenylboronic acid (2eq.) was added to a solution of 5-bromo-[l,2,4]triazolo[l,5-a]pyridin-2-ylamine in dioxane/water (5:1) K2CO3 (2 eq.) and PdCl2dppf (cat.) were added to the mixture. The resultion mixture was subjected to macrowave: T: 1400C, 60 min, Wmax: 150, Pmax: 150 PSI. The crude of the reaction was diluted with water. The product was extracted with ethyl acetate (3 times). The organic layers were dried with MgSO4. The solvent was removed under high vacuum to afford a brown solid used in the next step without further purification.
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; ;