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

HRID 42614Notes

Reaction equation

HRID 42614 reaction equation
[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

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 178503412HCID 178503412, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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%)

Workup

  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

Sources & evidence

ORD record
ord-e62f7a73321c42128862a6bd293ac001
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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