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[ CAS No. 870-46-2 ] {[proInfo.proName]}

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Chemical Structure| 870-46-2
Chemical Structure| 870-46-2
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Product Details of [ 870-46-2 ]

CAS No. :870-46-2 MDL No. :MFCD00007593
Formula : C5H12N2O2 Boiling Point : -
Linear Structure Formula :(CH3)3COC(O)NHNH2 InChI Key :DKACXUFSLUYRFU-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :70091
Synonyms :

Calculated chemistry of [ 870-46-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.37
TPSA : 64.35 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.18
Log Po/w (WLOGP) : 0.38
Log Po/w (MLOGP) : 0.38
Log Po/w (SILICOS-IT) : -1.03
Consensus Log Po/w : 0.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.57
Solubility : 35.2 mg/ml ; 0.266 mol/l
Class : Very soluble
Log S (Ali) : -1.09
Solubility : 10.8 mg/ml ; 0.0814 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.44
Solubility : 48.3 mg/ml ; 0.366 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.76

Safety of [ 870-46-2 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P210-P240-P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P370+P378-P403+P233-P501 UN#:1325
Hazard Statements:H228-H302-H315-H319-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 870-46-2 ]

* 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 [ 870-46-2 ]

[ 870-46-2 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 7137-97-5 ]
  • [ 870-46-2 ]
  • [ 681261-72-3 ]
  • 2
  • [ 870-46-2 ]
  • [ 2991-28-8 ]
  • [ 1079843-62-1 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 3h; To a solution of 5.Og (31.6 mmol) of <strong>[2991-28-8]2,5-difluorobenzoic acid</strong> (1-1) in 2OmL of 1: 1 THF/DMF was added 4.39g (33.2 mmol) of t-butylcarbazate, 6.67g (34.8 mmol) of EDCI, and 50 mg of DMAP. After stirring for 3h at room temperature, the reaction was dumped into ice water and extracted three times with ether. The combined organic phases were washed two times with 10percent citric acid, two times with saturated NaHCO3, once with water, once with brine, and then dried over MgSO4. Concentration by rotary evaporation provided the BOC-protected acyl hydrazine as a white solid. To a solution of 1.5g (5.5 mmol) of this material in 20 mL of CH2Cl2, cooled to 00C, was added 10 mL of trifluoroacetic acid, and the resultant mixture was allowed to stir for 2 h at that temperature. The volatiles were removed by rotary evaporation, the residue was partitioned between EtOAc and aqueous NaHCO3, the layers were separated, and the aqueous phase was extracted two more times with EtOAc. The combined organic phases were washed twice with saturated NaHCO3, brine, dried over Na2SO4, and concentrated to provide 663mg (3.85 mmol) of 2,5-difluorobenzohydrazide (1-2) as a white solid. This material was dissolved in 30 mL of EtOH, and then 1.5 mL of HOAc was added, followed by 390 muL (3.85 mmol) of benzaldehyde. After stirring for Ih at room temperature, the solvents were removed by rotary evaporation, and the residue was triturated with Et2O to provide the imine as a white powder. A portion of this imine (225mg, 0.86 mmol) was dissolved in 3 mL of acetic anhydride and heated at 125 0C for 2h After cooling to room temperature, the volatiles were removed by rotary evaporation, the residue was dissolve in EtOAc, washed twice with saturated NaHCO3, water, dried over Na2SO4, and concentrated. The residue was then purified by column chromatography with a gradient of EtOAc in hexanes to provide (1-3) as a white solid. IH NMR (500 MHz, CDC13): delta 7.6 -7.4 (m, 6H), 7.2 (m, 2H), 7.1 (s, IH), 2.4 (s, 3H) ppm. HRMS (ES) calc'd M + H for C16H12F2N2O2: 303.0940; found 303.0926.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In tetrahydrofuran; N,N-dimethyl-formamide; for 16h; Step B: Preparation of <strong>[2991-28-8]2,5-difluorobenzoic acid</strong> hydrazide: To a solution of<strong>[2991-28-8]2,5-difluorobenzoic acid</strong> (3.5 g, 22 mmol) in THF/DMF (20 mL/20 mL) was added EDCI (4.7 g, 24 mmol), DMAP (50 mg) and NH2NHBoC (3.07 g, 23.2 mmol). After stirring for 16 hours, the reaction was quenched with water (30 mL) and diluted with EtOAc (30 mL). The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude Boc-protected product, which was then dissolved in DCM (60 mL) at 0 °C. TFA (50 mL) was added to the above DCM solution. After stirring for 2 hours, the reaction mixture was concentrated and the residue was dissolved in DCM (60 mL). The solution was washed with saturated NaHCO3 (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired crude product.
  • 3
  • [ 870-46-2 ]
  • [ 143879-80-5 ]
  • [ 1073973-12-2 ]
YieldReaction ConditionsOperation in experiment
22% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 100℃; for 3h; <strong>[143879-80-5]2,3,4-<strong>[143879-80-5]trifluorobenzonitrile</strong></strong> (3 g, 19 mmol), tert-butyl carbazate (4 g, 30 mmol) and Hunig's base were dissolved in dioxane (10 mL) and heated at 100° C. for 3 d. The mixture was concentrated and then partitioned between toluene (25 mL) and water (29 mL). The toluene layer was added to a column and chromatographed (silica gel, 10 to 40percent ethyl acetate in hexanes) to give product as an oil. Recrystallization from ethyl acetate/hexanes gave N'-(4-cyano-2,3-difluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.16 g, 22percent) as a white powder. A second crop (0.5 g, 10percent) was obtained as a slightly pinkish powder. LCMS (m/z): M+H=170.1 (loss of BOC).
  • 4
  • [ 870-46-2 ]
  • [ 4385-76-6 ]
  • [ 1160395-83-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 1h; 4-Pyridin-4-yl benzoic acid (250mug, 1.25mmol), EDAC (288mug, 1.51 mmol), HOBt (227mug), and 1 ,1-dimethylethyl hydrazinecarboxylate (199mug), in DMF were stirred at <n="29"/>room temperature for 1 h. The reaction mixture was diluted with water (20mul), extracted with ethyl acetate (30mul x 3), the organic phase washed with bicarbonate, dried over magnesium sulfate and evaporated to give an oil, 520mg. This was used without further purification.
  • 5
  • [ 870-46-2 ]
  • [ 437-86-5 ]
  • [ 1075282-02-8 ]
YieldReaction ConditionsOperation in experiment
80% In dimethyl sulfoxide; at 100℃; for 0.166667h;Microwave irradiation; Stage 1: tert-butyl N-(2-methyl-6-nitro-phenyl)-hydrazino-carboxylate To 250 mg of 2-fluoro-3-methyl-nitrobenzene in 5 mL of DMSO are added 1.065 g of commercial tert-butoxycarbonylhydrazine (5 equivalents). The whole is brought to 100° C. for 10 min under microwave heating. The medium is hydrolyzed and then extracted with ethyl acetate several times. The organic phases are collected, dried on magnesium sulfate, filtered and evaporated under reduced pressure leading to a residue which is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). 342 mg of product corresponding to the expected product are obtained. Yield: 80percent 1H NMR (CDCl3, 250 MHz) delta (ppm): 7.86 (d, 1H), 7.35 (d, 1H), 6.97 (t, 1H), 6.40 (s broad, 1H), 1.34 (s broad, 9H)
  • 6
  • [ 870-46-2 ]
  • [ 65632-62-4 ]
  • [ 439292-93-0 ]
  • 7
  • [ 870-46-2 ]
  • [ 149437-76-3 ]
  • [ 1235493-23-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 50℃; for 16h; A mixture of tert-butyl hydrazinecarboxylate (1.45 g, 11.0 mmol) and <strong>[149437-76-3]5-(4-fluorophenyl)-5-oxopentanoic acid</strong> (2.1 g, 10 mmol) in THF (20 mL) was stirred at 50 0C for 16 h. The reaction mixture was concentrated in vacuo to afford 5-(2-(tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid (3.2 g, 9.87 mmol, 99 % yield). LC-MS (M+H)+ 325.24. The crude product was used for subsequent chemistry without purification.
  • 8
  • [ 3973-08-8 ]
  • [ 870-46-2 ]
  • [ 1254073-60-3 ]
YieldReaction ConditionsOperation in experiment
1 ,3-thiazole-4-carboxylic acid (0.775 g, 6 mmol, commercially available from e.g. Sigma-AIdrich, Apollo or Fluorochem) was dissolved in dichloromethane (DCM) (50 ml_), and the solution was cooled to 0 0C. To this was added oxalyl chloride (0.578 ml_, 6.60 mmol) and 5 drops of DMF (cat.) and the solution was stirred, under argon, for 3 hours. The solvent was then removed in vacuo, and the remaining residue was redissolved in dichloromethane (DCM) (50 ml_), before 1 ,1-dimethylethyl hydrazinecarboxylate (0.872 g, 6.60 mmol) and DIPEA (1.258 ml_, 7.20 mmol) were added. The solution was stirred under argon for 2 hours, LCMS and TLC confirmed product formation, thus the solvent was evaporated in vacuo. The remaining residue was then partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (20 ml). The aqueous phase was then further extracted with ethyl acetate (2 x 30 mL) and the combined extracts were washed with brine (30 mL), and dried over anhydrous sodium sulfate. The solvent was then evaporated in vacuo to yield the product in 1.308 g.
  • 9
  • [ 14190-59-1 ]
  • [ 870-46-2 ]
  • [ 1254073-54-5 ]
YieldReaction ConditionsOperation in experiment
EDC (742 mg, 3.87 mmol) and HOBt (593 mg, 3.87 mmol) were added to a suspension of 1 ,3-<strong>[14190-59-1]thiazole-2-carboxylic acid</strong> (500 mg, 3.87 mmol) in dry Dichloromethane (DCM) (19 ml) - solution became clear after the addition of EDC. The mixture was stirred at room temperature for 30 mins. 1 ,1-dimethylethyl hydrazinecarboxylate (512 mg, 3.87 mmol) was added and the resulting mixture was stirred at room temperature 1 day. The reaction mixture was diluted in DCM (150 mL) and washed with sat. NaHCOo (2 x 25 mL) and brine (25 mL). The resulting organic layer was dried over MgSpsi4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (10percent MeOH in DCM / DCM - 10CV) to afford desired product in 432.9 mg as an orange oil. LCMS m/z 243.9 [M+H] (at) 0.66 min (2 min run)
  • 10
  • [ 870-46-2 ]
  • [ 402-69-7 ]
  • [ 1254073-98-7 ]
YieldReaction ConditionsOperation in experiment
6-Fluoro-2-pyridinecarboxylic acid (2.83 g, 20.06 mmol, CAS[402-69-7], commercially available e.g. from Sigma-Aldrich or Apollo Scientific) was dissolved inDichloromethane (DCM) (100 ml.) at 0 0C. Oxalyl chloride (2.107 ml_, 24.07 mmol) and a drop of Lambda/,Lambda/-dimethylformamide (DMF) was added and the mixture was stirred for 2 hours. The solvents were removed in vacuo and azeotroped with toluene (3x20ml). The residue was dissolved in dichloromethane (DCM) (100 ml) whereupon 1 ,1-dimethylethyl hydrazinecarboxylate (2.92 g, 22.06 mmol) and Lambda/,Lambda/-diisopropylethylamine (DIPEA) (7.71 ml_, 44.1 mmol) were added. The mixture was stirred at room temperature for 3 hours and concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml). The aqueous phase was extracted with ethyl acetate (3x100ml), the combined organic extracts were washed with brine (50 ml), were dried over anhydrous sodium sulphate and were concentrated in vacuo. The residue was purified by flash chromatography (Biotage SP4, 40+M, 0-100percent ethyl acetate/iso- hexane) to afford 1 ,1-dimethylethyl 2-[(6-fluoro-2- pyridinyl)carbonyl]hydrazinecarboxylate (5.04 g, 19.75 mmol).LC/MS = 156 (M+H-BOC)+, retention time = 0.81 minutes (2 minute method).
  • 11
  • [ 22929-52-8 ]
  • [ 870-46-2 ]
  • [ 158020-60-1 ]
YieldReaction ConditionsOperation in experiment
95% In methanol; at 15℃; for 2h; A solution of <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (5.0 g, 58 mmol) and tert-butyl hydrazinecarboxylate (7.68 g, 58.08 mmol) in MeOH (50 mL) was stirred at 15° C. for 2 hours. The mixture was concentrated to remove MeOH and afford tert-butyl 2-(dihydrofuran-3(2H)-ylidene)hydrazine-1-carboxylate (11 g, 55 mmol, 95percent yield). 1H NMR (MeOD 400 MHz): delta4.19 (s, 2H), 4.03 (t, J=6.8 Hz, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.50 (s, 9H).
85% In methanol; at 20℃; for 2h; General procedure: A 100 mL 3-neck flask with inert gas valve and septum was charged with (6.50 g, 49.04 mmol) tert-butylhydrazinecarboxylate and 30 mL MeOH. (4.91 g, 49.04 mmol) dihydro-2H-pyran-3(4H)-one was syringed into the flask. The mixture was stirred at rt for 2 h to observe the disappearance of tert-butylhydrazinecarboxylate monitored by LC-MS. The mixture was then dried over Na2SO4 and the solution was filtered and the solvent removed under reduced pressure to yield 10.4 g of white solid (99percent yield). The compound was further purified by passing through a short silica pad using 50percent EtOAc in hexanes.
27.3 g In methanol; at 10 - 35℃; for 12h; (1) Synthesis of t-butyl 2-[dihydrofuran-3(2H)-ylidene]hydrazinecarboxylate 3-oxotetrahydrofuran (10.38 g) was dissolved in methanol (200 mL), and t-butyl carbazate (17.53 g) was added to the solution. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated to give the title compound (27.3 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.52 (s, 9H), 2.46 (t, J=6.9 Hz, al), 4.10 (t, J=6.9 Hz, 2H), 4.33 (s, 2H).
1.95 mmol In ethanol;Reflux; To a solution of dihydro(3(2H)-furanone (1 .95 mmol) in ethanol(2 mL) was added tert-butyl carbazate (2.35 mmol) and the reaction was heated to reflux and stirred overnight. Volatiles were removed under reduced pressure to give the titled compound (1.95 mmol) as a white solid. 1H NMR (400 MHz,CDCI3, 3, mixture of isomers): 7.25 (5, 0.75H), 7.12 (5, 0.25 H), 4.34 (t, J= 1.2 Hz, i.5H), 4.24 (t, J=1.2 Hz, 0.5H), 4.12 (t, J = 6.9 Hz, 1 .5H), 4.02 (t, J = 6.9 Hz, 0.5H), 2.78 (td, J = 6.9, 1.2 Hz, 0.5H), 2.48 (td, J = 6.9, 1.2 Hz, 1 .5H), 1.54 (5, 7.5H), 1.53 (5, 1 .5H).

  • 13
  • [ 870-46-2 ]
  • [ 119072-55-8 ]
  • [ 19230-50-3 ]
  • [ 78-84-2 ]
  • [ 1373025-47-8 ]
YieldReaction ConditionsOperation in experiment
77% General procedure: To 292 mg (4 mmol) of isobutyraldehyde in 4 ml of MeOH, 530 mg (4 mmol)of tert-butylcarbazatare added and the mixture is stirred at rt for 2 h. Then 1011 mg (4 mmol) of o-iodobenzoic acid and 339 mg (4 mmol) of tert-butylisocyanidare added and the reaction mixture is stirred overnight at rt. After evaporation of the solvent the crude product is purified by column chromatography on silica gel (chloroform/methanol = 99.5/0.5?90/10, Rf = 0.20 [chloroform/methanol = 99.5/0.5]) to yield 1.52 g of the title compound (white solid, 73%).
  • 14
  • [ 870-46-2 ]
  • [ 119072-55-8 ]
  • [ 54413-93-3 ]
  • [ 78-84-2 ]
  • [ 1373025-40-1 ]
YieldReaction ConditionsOperation in experiment
95% General procedure: To 292 mg (4 mmol) of isobutyraldehyde in 4 ml of MeOH, 530 mg (4 mmol)of tert-butylcarbazatare added and the mixture is stirred at rt for 2 h. Then 1011 mg (4 mmol) of o-iodobenzoic acid and 339 mg (4 mmol) of tert-butylisocyanidare added and the reaction mixture is stirred overnight at rt. After evaporation of the solvent the crude product is purified by column chromatography on silica gel (chloroform/methanol = 99.5/0.5-->90/10, Rf = 0.20 [chloroform/methanol = 99.5/0.5]) to yield 1.52 g of the title compound (white solid, 73percent).
  • 15
  • [ 94201-40-8 ]
  • [ 870-46-2 ]
  • ([(tert-butoxy)carbonyl]amino}amino)(1-phenylpiperidin-4-yl)methanone [ No CAS ]
  • 16
  • [ 870-46-2 ]
  • [ 582-80-9 ]
  • tert-butyl 2-(4-benzamidobenzoyl)hydrazinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 18h; The p-benzamido-benzoic acid (0.325 g, 1.3 mmol, 1.0 equiv.) and tert-butyl carbazate (0.160 g, 1.2 mmol, 0.9 equiv.) were dissolved in 6 ml of 1:1 DMF:THF at room temperature. The EDCI (0.284 g, 1.5 mmol, 1.1 equiv.) was added followed by catalytic amount of DMAP. The reaction was stirred for 18 hrs. The reaction was poured into saturated bicarb and the aqueous solution was extracted with EtOAc (3x). The combined organic layers were washed with H2O, 10percent HCl, H2O, brine, dried over Na2SO4 and concentrated in vacuo. tert-butyl 2-(4-benzamidobenzoyl) hydrazinecarboxylate (0.465 g, 1.31 mmol) was obtained as an off-white in 97percent yield.1H-NMR (400 MHz; DMSO-d6): delta 10.48 (s, 1H), 10.10 (s, 1H), 8.86 (s, 1H), 7.96 (dd, J = 8.3, 1.4 Hz, 2H), 7.90-7.85 (m, 4H), 7.63-7.59 (m, 1H), 7.56-7.53 (m, 2H), 1.43 (s, 9H); 13C NMR (101 MHz; DMSO-d6): delta 165.9, 165.4, 155.6, 142.2, 134.7, 131.8, 128.4, 128.1, 127.7, 119.5, 79.1, 28.10, 28.07; LC/MS (APCI) m/z calcd. for C19H20N3O4 [M?H]?: 354.2, found: 354.0
  • 17
  • [ 870-46-2 ]
  • [ 2592-18-9 ]
  • C14H27N3O6 [ No CAS ]
  • 18
  • [ 15855-06-8 ]
  • [ 870-46-2 ]
  • tert-butyl 2-(2-chloro-6-methoxyisonicotinoyl)hydrazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of <strong>[15855-06-8]2-chloro-6-methoxyisonicotinic acid</strong> (19) (188mg, 1.0mmol) in dichloromethane (10mL) was added oxalyl chloride (381mg, 3.0mmol) and 3 drops of DMF as catalyst. The mixture was stirred at room temperature for 1h and the solvent and excess oxalyl chloride was removed under vacuum. The residue was dissolved in the dichloromethane. To the solution was added tert-butyl hydrazinecarboxylate (132mg, 1.0mmol) and triethylamine (303mg, 3.0mmol) at 0C. The mixture was stirred at room temperature until the reaction was completed as determined by TLC. Then, the mixture was washed with water, saturated brine, and dried over anhydrous MgSO4. After filtration and concentration, the crude product was collected. 1H NMR (400MHz, DMSO-d6) delta 10.50 (s, 1H, -OCONH), 9.08 (s, 1H, CONH), 7.42 (s, 1H, Ar-H), 7.19 (s, 1H, Ar-H), 3.90 (s, 3H, -O-CH3), 1.43 (s, 9H, -C-CH3).
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Similarity: 0.78

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