Acetyl chloride → N-[5-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetamide

HRID 42614노트

반응식

HRID 42614 반응식
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)=[C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[CH:9]=2)[NH:4][N:3]=1.[C:29](Cl)(=[O:31])[CH3:30]>N1C=CC=CC=1>[CH3:18][S:17][C:13]1[N:12]=[C:11]([C:8]2[CH:9]=[C:10]3[C:2]([NH:1][C:29](=[O:31])[CH3:30])=[N:3][NH:4][C:5]3=[N:6][C:7]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[CH:16]=[CH:15][N:14]=1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 178503412HCID 178503412, 화합물

생성물 1

HCID 10478615N-[5-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetamide수율 37%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of 3-amino-5-[2-(methylsulfanyl)pyrimidin-4-yl]-6-[3-(trifluoromethyl)phenyl]-1H-pyrazolo[3,4-b]pyridine (200 mg, 0.5 mmol, obtained in example 123) and acetyl chloride (39 mg, 0.5 mmol) in pyridine (10 mL) was stirred at room temperature for 3 h. It was concentrated and the residue was taken up in a mixture of EtOAc and 1 N NaOH. The organic phase was dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 78 mg of the title compound (yield: 37%)

후처리

  1. concentrationIt was concentrated
  2. additionthe residue was taken up in a mixture of EtOAc and 1 N NaOH
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe crude product obtained
  6. customwas purified by chromatography on silica gel
  7. temperatureof increasing polarity as eluent

출처 및 근거

ORD 기록
ord-e62f7a73321c42128862a6bd293ac001
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536194B2

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