Ammonium Hydroxide → 2-(3-(5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetamide

HRID 1696452Notes

Reaction equation

HRID 1696452 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14](OCC)=[O:15])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[CH:3]=1.[NH4+:23].[OH-]>>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]([NH2:23])=[O:15])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[CH:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 67272221HCID 67272221, compound

Product 1

HCID 672707762-(3-(5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetamideYield 66%

Procedure

A solution of ethyl 2-(3-(5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetate (3 g, 9.58 mmol) in conc. NH4OH (40 mL) was heated at reflux for 2 h. After removal of the solvent, the residue was purified by column chromatography to afford 2-(3-(5-amino-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)acetamide (1.8 mg, 66% yield). 1H NMR (300 MHz, DMSO-d6): 7.48-7.42 (m, 4H), 7.30 (s, 1H), 6.91 (s, 1H), 5.77 (s, 1H), 5.73-5.72 (m, 2H), 4.44 (s, 2H). MS (ESI) m/z: 285 (M+H+).

Workup

  1. temperatureat reflux for 2 h
  2. customAfter removal of the solvent
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-05060a9b21614e5db74e8aa9ac2b78bf
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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