Potassium Carbonate → phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate

HRID 631700노트

반응식

HRID 631700 반응식
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([C:13]3([C:16]([F:19])([F:18])[F:17])[CH2:15][CH2:14]3)=[N:8]2)=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:28]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:29]>C(Cl)Cl>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([N:7]2[C:11]([NH:12][C:28](=[O:29])[O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:10][C:9]([C:13]3([C:16]([F:18])([F:19])[F:17])[CH2:15][CH2:14]3)=[N:8]2)=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

생성물 1

HCID 66876638phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate수율 129.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (574 mg, 2.0 mmol) in DCM (20 mL) was added K2CO3 (423 mg, 3.06 mmol) and phenyl chloroformate (386 μL, 3.06 mmol). The solution was stirred at rt overnight. The reaction mixture was filtered and the solids washed with DCM, the filtrate concentrated and purified using silica gel chromatography eluting with an EtOAC/Hexane gradient (5-20%) to give phenyl 1-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-ylcarbamate (1.04 g, quantitative yield). 1H NMR (300 MHz, DMSO d6) δ 1.33 (m, 4H), 2.34 (s, 3H), 6.51 (s, 1H), 7.12 (m, 2H), 7.23 (m, 1H), 7.37 (m, 6H), 10.13 (s, 1H); LC-MS (ESI) m/z 402 (M+H)+

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with DCM
  3. concentrationthe filtrate concentrated
  4. custompurified
  5. washeluting with an EtOAC/Hexane gradient (5-20%)

출처 및 근거

ORD 기록
ord-881dddbd9074421a94d8b9f839a61b72
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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