Dimethylformamide → 4-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl)-1H-pyrazole-3-carboxamide

HRID 639973Notes

Reaction equation

HRID 639973 reaction equation
O.NN.[F:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:25])[CH2:13][N:14]2[CH:18]=[C:17]([N+:19]([O-])=O)[C:16]([C:22]([NH2:24])=[O:23])=[N:15]2)[CH:8]=[CH:9][CH:10]=1.CN(C)C=O>[Ni].C(O)C>[NH2:19][C:17]1[C:16]([C:22]([NH2:24])=[O:23])=[N:15][N:14]([CH2:13][C:12]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([F:4])[CH:6]=2)=[O:25])[CH:18]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 686400711-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxamide

Product 1

HCID 686388614-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl)-1H-pyrazole-3-carboxamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.4 ml, 8.26 mmol) was slowly added to a mixture of 1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-4-nitro-1H-pyrazole-3-carboxamide (580 mg, 1.89 mmol) and Raney nickel (0.25 g) in ethanol (40 ml) at 50° C., and the mixture was stirred for 1 hour. Dimethylformamide was added to the mixture to solubilize the precipitated solid. The mixture was filtered, the filtrate was evaporated and the residue triturated with a mixture of dichloromethane and diethyl ether to yield 4-amino-1-{2-[(3-fluorophenyl)amino]-2-oxoethyl}-1H-pyrazole-3-carboxamide (430 mg, 81% yield):

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customthe residue triturated with a mixture of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-37e39bbd745f48198ed4a1bc0b31da5d
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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