Water → 3-Fluoro-4-(3-(2-pyridyl)-1-pyrazolyl)phenyl carbamic acid benzyl ester

HRID 1844505노트

반응식

HRID 1844505 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:10]1)[NH2:5].C(=O)([O-])[O-].[K+].[K+].[CH:26]1[CH:31]=[CH:30][C:29]([CH2:32][O:33][C:34](Cl)=[O:35])=[CH:28][CH:27]=1.O>ClCCl>[CH2:32]([O:33][C:34](=[O:35])[NH:5][C:4]1[CH:6]=[CH:7][C:8]([N:9]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:10]2)=[C:2]([F:1])[CH:3]=1)[C:29]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 867193713-fluoro-4-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)aniline

생성물 1

HCID 867193723-Fluoro-4-(3-(2-pyridyl)-1-pyrazolyl)phenyl carbamic acid benzyl ester수율 81.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The above-described product 19a (1 g, 3.9 mmol) was dissolved in dichloromethane (4 mL), and then anhydrous potassium carbonate (0.6 g) was added thereto. Then, Cbz-Cl (1.863 g, 1.537 mL) was slowly dropped, at a rate of 1-2 drops per second, into the mixture maintained in an ice-salt bath. The resultant mixture was reacted for 4 hours at room temperature. After completion of the reaction, water was added into the reaction mixture, followed by extraction with ethyl acetate. The combined ethyl acetate phase was evaporated in vacuum to get a crude product, which was recrystallized with acetone to afford the product 20a (1.235 g) as a white solid, with a yield of 80.8%.

후처리

  1. temperaturemaintained in an ice-salt bath
  2. additionwas added into the reaction mixture
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe combined ethyl acetate phase was evaporated in vacuum
  5. customto get a crude product, which
  6. customwas recrystallized with acetone

출처 및 근거

ORD 기록
ord-da71513000f3410ca597590bcbc90d6c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946436B2

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