Phenylhydrazine hydrochloride → 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

HRID 1917888노트

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HRID 1917888 반응식
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].Cl.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO.O>[C:14]1([N:20]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:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

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온도
90 °C

실험 절차

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), 1NaOH(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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8d96f4eef52e4f47affe6d344f222609
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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