Ethyl 2-(4-hydrazinylphenyl)acetate → {4-[5-Amino-3-(4-fluorophenyl)pyrazol-1-yl]phenyl}acetic acid ethyl ester

HRID 1696605Notes

Reaction equation

HRID 1696605 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1)[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][C:24]#[N:25])=[CH:18][CH:17]=1>>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:24]([NH2:25])=[CH:23][C:22]([C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=3)=[N:13]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 578093Ethyl 2-(4-hydrazinylphenyl)acetateHCID 2783172p-Fluorobenzoylacetonitrile

Product 1

HCID 58851779{4-[5-Amino-3-(4-fluorophenyl)pyrazol-1-yl]phenyl}acetic acid ethyl esterYield 68%

Procedure

Using general method M, (4-hydrazinophenyl)acetic acid ethyl ester (36 g, 0.217 mol) and 3-(4-fluorophenyl)-3-oxopropionitrile (38 g, 0.26 mol) were combined to yield {4-[5-amino-3-(4-fluorophenyl)pyrazol-1-yl]phenyl}acetic acid ethyl ester (50 g, 68% yield). 1H NMR (300 MHz, CDCl3): δ 7.80 (s, 2H), 7.40 (m, 4H), 7.00 (m, 2H), 6.29 (s, 1H), 4.07 (q, J=3.9 Hz, 2H), 3.53 (s, 2H), 1.23 (t, J=3.9 Hz, 3H); MS (ESI) m/z: 340 (M+H+).

Sources & evidence

ORD record
ord-dffb4f3ba5f241dc879fde9f3b7a7070
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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