反应详情

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-ethylphenyl}-3-(1-cyano-1-methylethyl)benzamide (270 mg, 0.59 mmol) in pyridine (6.0 mL) was added cyclopropanecarbonyl chloride (70 μL, 0.767 mmol), and the mixture was stirred at room temperature for 12 hr. Cyclopropanecarbonyl chloride (35 μL, 0.383 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was diluted with ethyl acetate (50 mL), washed with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and the obtained solution was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the title compound (188 mg, 61%) as a colorless powder.

1. stirringthe mixture was further stirred at room temperature for 1 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionthe obtained residue was diluted with ethyl acetate (50 mL)
4. washwashed with 5% aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (50 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
9. concentrationthe obtained solution was concentrated under reduced pressure
10. customThe residue was recrystallized from ethyl acetate