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

HRID 871487노트

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HRID 871487 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].[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

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 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), 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)+.

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-c034ce3447e849ba9367602ec7587283
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969587B2

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