Sodium Hydroxide → 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

HRID 631443Notes

Reaction equation

HRID 631443 reaction equation
O=[C:2]([C:6]1([C:9]([F:12])([F:11])[F:10])[CH2:8][CH2:7]1)[CH2:3][C:4]#[N:5].[OH-].[Na+].Cl.[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO.O>[C:16]1([N:22]2[C:4]([NH2:5])=[CH:3][C:2]([C:6]3([C:9]([F:10])([F:11])[F:12])[CH2:8][CH2:7]3)=[N:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 60962Phenylhydrazine hydrochlorideHCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

Product 1

HCID 668765051-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amineYield 43.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To 3-oxo-3-(1-(trifluoromethyl)cyclopropyl) propanenitrile (230 mg, 1.3 mmol) in EtOH (5 mL, 200 proof) was added H2O (3.7 mL), 1N NaOH(aq) (1.3 mL), and phenylhydrazine hydrochloride (188 mg, 1.3 mmol) and the mixture heated at 90° C. overnight. After cooling to room temperature, the mixture was diluted with H2O, extracted with EtOAc, the org layer concentrated in vacuo, and purified by column chromatography (5-25% EtOAc/hexanes) to give 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (150 mg, 0.56 mmol, 43%). LC-MS (ESI) m/z 268 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. concentrationthe org layer concentrated in vacuo
  4. custompurified by column chromatography (5-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-831c7112782246aabf69d1e0bf6fdf06
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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