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[ CAS No. 71574-33-9 ] {[proInfo.proName]}

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Chemical Structure| 71574-33-9
Chemical Structure| 71574-33-9
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Quality Control of [ 71574-33-9 ]

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Product Details of [ 71574-33-9 ]

CAS No. :71574-33-9 MDL No. :MFCD00012711
Formula : C5H9ClN2S Boiling Point : -
Linear Structure Formula :- InChI Key :XYTUTNQRQLAZLK-UHFFFAOYSA-N
M.W : 164.66 Pubchem ID :16211387
Synonyms :

Calculated chemistry of [ 71574-33-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.42
TPSA : 67.15 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 0.59
Log Po/w (SILICOS-IT) : 2.24
Consensus Log Po/w : 1.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.357 mg/ml ; 0.00217 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.0916 mg/ml ; 0.000556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.67
Solubility : 3.52 mg/ml ; 0.0214 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.26

Safety of [ 71574-33-9 ]

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

Application In Synthesis of [ 71574-33-9 ]

* 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 [ 71574-33-9 ]

[ 71574-33-9 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 2289-75-0 ]
  • [ 71574-33-9 ]
  • [ 99168-88-4 ]
  • 2
  • [ 71574-33-9 ]
  • [ 2094-72-6 ]
  • [ 377063-72-4 ]
YieldReaction ConditionsOperation in experiment
74% To a solution of 4,5~dimethyl-ihiazo3-2-ylamine hydrochloride (1 65 g, 10 0 mmol) in TetaF (100 mL) was added tiiethylamine (4 2 mL, 30 mmol) and adamantane-l-carbonyl chloride (2 2 g, 1 1 mmol) The mixture was heated at reflux overnight and then concentrated under reduced pressure The residue was diluted with ethyl acetate, washed with IM NaHCO3, dried (Na2SO4), filtered and concentrated Purification by column chromatography (SiO2, 10 %ethyl acetate: 90% hexanes) afforded 2 15 g (74%) of the title compound MS (ESI+) m/z 291 (M+H)+
  • 3
  • [ 1899-93-0 ]
  • [ 71574-33-9 ]
  • N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% m-Toluenesulfonyl chloride (0.076 ml, 0.53 mmol, 1.4 equiv.) and pyridine (0.103 ml, 1.27 mmol, 3.4 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 3 hours. 2-Amino-4,5-dimethylthiazole hydrochloride (34 mg, 0.28 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was centrifuged for 10 minutes and the supernatant decanted. The solid washed with water (2 ml), the material centrifuged and supernatant decanted. The solid was dried under reduced pressure at 40 C. to give N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide, 49 mg (55% yield). LC aUV215 nm; Rt 1.81: 93%, m/z (ES+): 326 (MH+), 651 (2 MH+); deltaH(400 MHz; d4-methanol) 7.54-7.98 (4H, m), 2.57 (3H, s), 2.31 (3H, s), 2.27 (3H, s).
  • 4
  • [ 3095-95-2 ]
  • [ 71574-33-9 ]
  • 2-[(N-diethylphosphonoacetyl)amino]-4,5-dimethylthiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; Step M. A solution of <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (2 mmole) and diethyl phosphonoacetica acid (1 mmole) in DMF (5 ML) was treated with EDCI (1.5 mmole), HOBt (1.5 mmole) and triethylamine (2 mmole) at room temperature for 24 h.. The reaction was subjected to evaporation, extraction and chromatography to give 2-[(N-diethylphosphonoacetyl)amino]-4,5-dimethylthiazole as a yellow solid, which was subjected to Step D of Example 18 followed by Step C of Example 3 to give 4,5-dimethyl-2-[(N-phosphonoacetyl)amino]thiazole (18.7) as a light brown solid. Mp>250 C. Anal. Calcd. for C7H11N2O4PS: C: 33.60; H: 4.43; N: 11.20. Found: C: 33.62; H: 4.29; N: 10.99.
  • 5
  • [ 66493-39-8 ]
  • [ 71574-33-9 ]
  • [4-(4,5-dimethyl-thiazol-2-ylcarbamoyl)-phenyl]-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20℃; 4-tert-Butoxycarbonylamino-benzoic acid (6.3 mmol) and 1-hydroxybenzotriazole (6.3 mmol) were combined in a flask and suspended in 1, 2-dichloroethane (30 mL). 1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (6.3 mmol) and DIPEA (15.4 mmol) was added followed by 4, 5-dimenthyl-2-amino-thiazole hydrochloride (9.1 mmol). The resulting solution was stirred at ambient temperature over night, then the reaction mixture was washed extensively with AcOH (aq. , pH -3), dried over MgS04, filtered and evaporated. During evaporation of the solvent the desired product precipitated and was collected by filtration, washed with 1,2- dichloroethane and dried. Yield: 20% 1H NMR (D6-DMSO) : 1.50 (s, 9H); 2.20 (s, 3H); 2.26 (s, 3H) ; 7. 58 (d, 2H); 8.02 (d, 2H); 9.73 (s, 1H) ; 12.20 (br s, 1H).
  • 6
  • [ 32315-10-9 ]
  • [ 71574-33-9 ]
  • [ 286371-71-9 ]
  • [ 475108-60-2 ]
YieldReaction ConditionsOperation in experiment
42% With triethylamine; In chloroform; water; Example 45 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-phenyl}-N'-(4,5-dimethyl-1,3-thiazol-2-yl)urea 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (40 mg) was dissolved in chloroform (1.2 ml) and triethylamine (0.2 ml) to prepare a solution. A solution of triphosgene (20 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 5 min. Next, <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (24 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was concentrated, and the residue was then purified by chromatography (chloroform:acetone=2:1) to give the title compound (25.8 mg, yield 42%). 1H-NMR (DMSO-d6, 400 MHz): delta 2.12 (s, 3H), 2.21 (s, 3H), 3.98 (d, J=5.1 Hz, 6H), 7.24 (d, J=8.8 Hz, 2H), 7.38 (s, 1H), 7.56 (s, 1H), 7.57 (d, J=7.3 Hz, 2H), 8.54 (s, 1H) Mass spectrometry value (ESI-MS, m/z): 450 (M+-1)
  • 7
  • [ 286371-63-9 ]
  • [ 32315-10-9 ]
  • [ 71574-33-9 ]
  • [ 475108-55-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In chloroform; water; acetone; Example 40 N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(4,5-dimethyl-1,3-thiazol-2-yl)urea 2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (100 mg) was dissolved in chloroform (5 ml) and triethylamine (0.5 ml) to prepare a solution. A solution of triphosgene (100 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 15 min. Next, <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (50 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Distilled water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine and was dried over sodium sulfate. The organic layer was concentrated under the reduced pressure, and the residue was purified by HPLC using chloroform/acetone for development to give 33 mg of the title compound. 1H-NMR (CDCl3, 400 MHz): delta 8.61 (1H, s), 8.48 (1H, d, J=9.0 Hz), 7.51 (1H, s), 7.34 (1H, d, J=2.7 Hz), 7.31 (1H, s), 7.17 (1H, dd, J=2.7 Hz, J=9.0 Hz), 4.05 (3H, s), 4.05 (3H, s), 2.26 (3H, s), 2.24 (3H, s) Mass spectrometry value (ESI-MS, m/z): 484 (M+-1)
  • 8
  • 3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline [ No CAS ]
  • [ 32315-10-9 ]
  • [ 71574-33-9 ]
  • [ 475108-64-6 ]
YieldReaction ConditionsOperation in experiment
68% With triethylamine; In diethyl ether; chloroform; water; Example 49 N-{3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(4,5-dimethyl-1,3-thiazol-2-yl)urea 3-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (84 mg) was dissolved in chloroform (2.5 ml) and triethylamine (0.50 ml) to prepare a solution. A solution of triphosgene (38 mg) in chloroform was then added to the solution, and the mixture was stirred at room temperature for 5 min. Next, <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (42 mg) was added thereto, and the mixture was further stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was subjected to separatory extraction with chloroform. The organic layer was concentrated and was evaporated to dryness. Diethyl ether was then added to the solid, and the solid was collected by filtration. Further, the collected solid was washed with methyl alcohol to give the title compound (86.4 mg, yield 68%). 1H-NMR (DMSO-d6, 400 MHz): delta 2.13 (s, 3H), 2.20 (s, 3H), 3.99 (d, J=5.9 Hz, 6H), 7.38-7.49 (m, 3H), 7.57 (s, 1H), 7.88 (br, 1H), 8.54 (s, 1H) Mass spectrometry value (ESI-MS, m/z): 484 (M+-1)
  • 9
  • [ 71574-33-9 ]
  • [ 4637-24-5 ]
  • [ 174208-87-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In toluene; PREPARATION 1 N'-(4,5-Dimethyl-2-thiazolyl)-N,N-dimethyl-methanimidamide (Formula A-2) Refer to Chart A. A suspension of <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (4.92 g, 30 mmol) (Formula A-1) in toluene (60 mL) was treated with triethylamine (4.5 mL, 35 mmol) and vigorously stirred for 30 minutes. The mixture was treated with dimethylformamide dimethyl acetal (7.3 mL, 60 mmol) and heated at reflux temperature for 2 hours. The solution was cooled, diluted with ethyl acetate, washed with saline, dried and evaporated. The residue was crystallized from hexane to provide pure N'-(4,5-Dimethyl-2-thiazolyl)-N,N-dimethyl-methanimidamide (Formula A-2) (4.31 g, 77%), m.p. 47-58. Anal. Calc'd for C8H13N3S: C, 52.42; H, 7.14; N, 22.92; S, 17.49. Found: C, 52.31; H, 7.27; N, 22.87; S, 17.65. MS m/z 183 (M+), 168, 150, 141, 113, 98, 86, and 71. NMR (CDCl3) 2.22 (s, 3, CH3), 2.26 (s, 3, CH3), 3.10 (s, 6, CH3), 8.10 (s, 1, CH).
  • 10
  • 3-(2-amino-quinazolin-6-yl)-4-methyl-benzoyl chloride [ No CAS ]
  • [ 71574-33-9 ]
  • 3-(2-amino-6-quinazolinyl)-N-(4,5-dimethyl-1,3-thiazol-2-yl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 15h; 3-(2-Aminoquinazolin-6-yl)-4-methylbenzoic acid (0.060 g, 0.21 mmol) was suspended in neat thionyl chloride (0.5 ml) at ambient temperature. The mixture was heated at reflux for 1 h, then cooled to ambient temperature. The resulting solution was concentrated in vacuo, then diluted with toluene and concentrated a second time. The crude solid was dried under high vacuum for 0.5 h. To a solution of the crude solid in anhydrous methylene chloride (2.1 ml), was added <strong>[71574-33-9]2-amino-4,5-dimethylthiazole hydrochloride</strong> (0.036 g, 0.21 mmol) and triethylamine (0.15 ml, 1.10 mmol). The solution was stirred at ambient temperature for 15 h then concentrated in vacuo. Purification by silica chromatography (5% methanol/methylene chloride) afforded 3-(2-amino-6-quinazolinyl)-N-(4,5-dimethyl-1,3-thiazol-2-yl)-4-methylbenzamide as a white solid. MS (M+H+) 390.2; Calculated for C21H19N5OS: 389.
  • 11
  • [ 939039-44-8 ]
  • [ 71574-33-9 ]
  • [ 939039-45-9 ]
YieldReaction ConditionsOperation in experiment
44% In o-xylene; at 150℃; for 18h; Procedure 18; [00219] A solution of (5-chloropyridin-2-yl)(3-fluoro-5- (trifluoromethyl)phenyl)methanimine (1.7 g, 5.6 mmol) and 4,5-dimethylthiazol-2- amine HCl salt (900 mg, 5 mmol) in o-xylene (10 mL) was heated at 150 0C for 18 h, then allowed to cool to room temperature. The solvent was removed under reduced pressure and the residue purified by ISCO chromatography (80 g column) using hexanes/EtOAc (0-40%) over 25 min to give (E)-N-((5-chloropyridin-2-yl)(3-fiuoro- 5-(trifluoromethyl)phenyl)methylene)-4,5-dimethylthiazol-2-amine as a beige solid (910 mg, 44% yield). LCMS RT = 4.00 min [M+H] 413.87 (Phenomenex Luna C18 column, 4.6 x 50 mm eluting with 10-90% MeOHTH2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).
  • 12
  • [ 946132-90-7 ]
  • [ 71574-33-9 ]
  • 2-[{4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-3-methylphenyl}(ethyl)-amino]-N,N,N-trimethylethanaminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Example 1b 2-[{4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-3-methylphenyl}(ethyl)amino]-N,N,N-trimethylethanaminium bromide Analogously to the procedure described in example 1a, by azocoupling of 2-amino-4,5-dimethyl-1,3-thiazol hydrochloride with 2-[ethyl(3-methylphenyl)amino]-N,N,N-trimethylethanaminium bromide to give 2-[{4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-3-methylphenyl}(ethyl)amino]-N,N,N-trimethylethanaminium bromide in 55 % yield. 1H NMR (300 MHz, DMSO): delta = 7.70 (d, J=9.0, 1H, H(5)-phenyl); 6.77 (dd, J=9.0, J=2.7,1H, H(6)-phenyl); 6.75 (d, J=2.7,1H, H(2)-phenyl); 3.90 (m, 2H, N+CH2); 3.52 (m, 4H, 2 x NCH2); 3.21 (s, 9H, 3xCH3); 2.57 (s, 3H, CH3); 2.37 (s, 3H, CH3); 2.31 (s, 3H, CH3); 1.18 (t, J=6.9, 3H, CH3).
  • 13
  • 2-[(3-chlorophenyl)-(ethyl)amino]-N,N,N-trimethylethanaminium methyl sulfate [ No CAS ]
  • [ 71574-33-9 ]
  • 2-[{3-chloro-4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)-amino]-N,N,N-trimethylethanaminium methyl sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Example 1c 2-[{3-chloro-4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]-phenyl} (ethyl)amino]-N,N,N-trimethylethanaminium methyl sulfate Analogously to the procedure described in example 1a, by azocoupling of 2-amino-4,5-dimethyl-1,3-thiazol hydrochloride with 2-[(3-chlorophenyl)-(ethyl)amino]-N,N,N-trimethylethanaminium methyl sulfate to give 2-[{3-chloro-4-[(4,5-dimethyl-1,3-thiazol-2-yl)diazenyl]phenyl}(ethyl)-amino]-N,N,N-trimethylethanaminium methyl sulfate in 44 % yield. 1H NMR (300 MHz, DMSO): delta = 7.78 (d, J=9.3, 1H, H(5)-phenyl); 7.00 (d, J=2.4, 1H, H(2)-phenyl); 6.90 (dd, J=9.0, J=2.7, 1H, H(6)-phenyl); 3.92 (m, 2H, N+CH2); 3.55 (m, 4H, 2 x NCH2); 3.19 (s, 9H, 3xCH3); 2.39 (s, 3H, CH3); 2.33 (s, 3H, CH3); 1.18 (t, J=6.9, 3H, CH3).
  • 14
  • [ 54902-24-8 ]
  • [ 71574-33-9 ]
  • N-[2,2-dichloro-1-(4,5-dimethyl-1,3-thiazol-2-ylcarbamoyl)vinyl]benzamide [ No CAS ]
  • 15
  • [ 61767-34-8 ]
  • [ 71574-33-9 ]
  • N-[2,2-dichloro-1-(4,5-dimethyl-1,3-thiazol-2-ylcarbamoyl)vinyl](4-methylbenzamide) [ No CAS ]
  • 16
  • [ 71574-33-9 ]
  • [ 1398750-23-6 ]
YieldReaction ConditionsOperation in experiment
Example 14 (3S)-2-((2R)-3-Cyclopentyl-2-[formyl(hydroxy)amino]methyl}propanoyl)-N-(4,5-dimethyl-1,3-thiazol-2-yl)-3-pyrazolidinecarboxamide <strong>[71574-33-9]2-amino-4,5-dimethyl thiazole hydrochloride</strong> (147 mg, 0.893 mmol). LC/MS: (M+H)+: 423.8.
  • 17
  • [ 5112-47-0 ]
  • [ 71574-33-9 ]
  • N-(4,5-dimethylthiazol-2-yl)-4-oxo-4H-chromene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Microwave irradiation; To a solution of chromone-2-carboxylic acid (0.5 g, 2.63 mmol) in DMF (4 mL), POCl3 (241 mul, 2.6 mmol) was added. The mixture was stirred at room temperature for 30 min, with in situ formation of the corresponding acyl chloride. Then N,N-diethylpropan-2-amine (459 mul, 2.63 mmol) and <strong>[71574-33-9]4,5-dimethylthiazol-2-amine hydrochloride</strong> (433 mg, 2.63 mmol) were added. The system was heated 120 C for 5 min in a microwave apparatus. After, the mixture was diluted with dichloromethane (20 mL), washed with H2O (2 * 10 mL) and with saturated NaHCO3 solution (2 * 10 mL). The organic phase was dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (50% AcOEt/n-hexane). N-(4,5-dimethylthiazol-2-yl)-4-oxo-4H-chromene-2-carboxamide as a yellow powder (Yield 40%). 1H NMR (CDCl3): delta = 2.26 (3H, s, CH3). 2.35 (3H, s, CH3), 7.27 (1H, s, H(3)), 7.44 (1H, d, J = 8.4 Hz, H(8)), 7.49 (1H, ddd, J = 8.0, 7.2, 1.0 Hz, H(6)), 7.76 (1H, ddd, J = 8.7, 7.2, 1.7 Hz, H(7)), 8.23 (1H, dd, J = 8.0, 1.5 Hz, H(5)). 13C NMR (CDCl3): delta = 11.0 (CH3), 14.3 (CH3), 113.3 (C3), 118.0 (C8), 122.0 (C3'), 124.4 (C4a), 126.2 (C5), 126.3 (C6), 134.9 (C7), 142.0 (C4'), 153.3 (C8a), 156.2 (C1'), 157.0 (C2, CONH) , 177.6 (C4). MS/EI m/z: 300 (M+?, 100), 272 (17), 199 (27), 163 (31), 139 (76), 101 (41).
  • 18
  • [ 32315-10-9 ]
  • (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine [ No CAS ]
  • [ 71574-33-9 ]
  • (9S)-N-(4,5-dimethylthiazol-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% To a solution of (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (600 mg, 2.253 mmol) in THF (15 mL) were added triethylamine (0.942 mL, 6.76 mmol) and triphosgene (334 mg, 1.126 mmol) at 30 C. and stirred for 1 h. Then <strong>[71574-33-9]4,5-dimethylthiazol-2-amine hydrochloride</strong> (556 mg, 3.38 mmol) was added at 30 C. and reaction was heated at 70 C. for 16 h. The solvent evaporated under reduced pressure, residue diluted with water (40 ml) and extracted with DCM (2×40 ml). The combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain crude compound. The crude mixture was purified by flash column chromatography and prep HPLC to afford (9S)-N-(4,5-dimethylthiazol-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (275 mg, 0.655 mmol, 42% yield) as a pale yellow solid (TLC: 10% MeOH in EtOAc, Rf: 0.3), LCMS (m/z): 421.27 [M+H]+. 1H NMR (400 MHz, CDCl3): delta ppm 14.79 (s, 2H), 8.64 (d, J=5.26 Hz, 2H), 8.02 (s, 1H), 7.64 (dd, J=5.26, 1.53 Hz, 1H), 7.54 (q, J=8.11 Hz, 1H), 4.99 (s, 1H), 3.42-3.18 (m, 3H), 3.12-2.89 (m, 1H), 2.79 (s, 3H), 2.28 (s, 3H), 2.22 (s, 3H), 2.00-1.75 (m, 1H), 1.52-1.35 (m, 2H).
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Chemical Structure| 3581-91-7

[ 3581-91-7 ]

4,5-Dimethylthiazole

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Chemical Structure| 1603-91-4

[ 1603-91-4 ]

4-Methylthiazol-2-amine

Similarity: 0.78

; ;