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

HRID 42614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 42614
[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

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 178503412HCID 178503412, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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%)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e62f7a73321c42128862a6bd293ac001
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536194B2

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