Diethyl Ether → 2-[3-(acetylamino)-4-amino-1H-pyrazol-1-yl]-N-(3-fluorophenyl)acetamide

HRID 639978Notes

Reaction equation

O.NN.[C:4]([NH:7][C:8]1[C:12]([N+:13]([O-])=O)=[CH:11][N:10]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[O:18])[N:9]=1)(=[O:6])[CH3:5].C(OCC)C>CC(N(C)C)=O.CO.[Pd]>[C:4]([NH:7][C:8]1[C:12]([NH2:13])=[CH:11][N:10]([CH2:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)=[O:18])[N:9]=1)(=[O:6])[CH3:5]

Participants

Conditions

Temperature: 75 °C

Procedure

Hydrazine hydrate (43.6 μl, 0.9 mmol) was slowly added to a solution of 2-[3-(acetylamino)-4-nitro-1H-pyrazol-1-yl]-N-(3-fluorophenyl)acetamide (0.145 g, 0.45 mmol) in a mixture of dimethylacetamide (3 ml) and methanol (3 ml) in the presence of 10% palladium on carbon (0.030 g). The mixture was stirred at 75° C. for 20 minutes and then allowed to cool. The mixture was filtered through Celite and the residue washed with methanol. The filtrate was evaporated and the residue triturated with a 1:2 mixture of dichloromethane:diethyl ether to give 2-[3-(acetylamino)-4-amino-1H-pyrazol-1-yl]-N-(3-fluorophenyl)acetamide (0.125 g, 95% yield):

Workup

temperatureto cool
filtrationThe mixture was filtered through Celite
washthe residue washed with methanol
customThe filtrate was evaporated
customthe residue triturated with a 1:2 mixture of dichloromethane

Sources & evidence

ORD record: ord-15523598146d4e31a302b665b18a7e85
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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