反应详情

To a solution of N-{5-[(2-amino[1,2,4]triazolo[1,5-a]pyridin-6-yl)oxy]-2-methylphenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide (158 mg, 0.419 mmol) and triethylamine (63.8 μL, 0.461 mmol) in tetrahydrofuran (5 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (41.9 μL, 0.461 mmol), and the mixture was stirred at room temperature for 1 hr. Cyclopropanecarbonyl chloride (83.8 μL, 0.922 mmol) was further added and the mixture was stirred for 1 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, sodium carbonate (200 mg), methanol (3 mL) and water (100 μL) were added to the residue, and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=50/50→0/100) and recrystallized from ethyl acetate to give the title compound (112 mg, 60%) as a white solid.

1. stirringthe mixture was stirred at room temperature for 1 hr
2. stirringthe mixture was stirred for 1 hr
3. extractionextracted with ethyl acetate
4. washThe organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltrated
7. concentrationThe filtrate was concentrated under reduced pressure, sodium carbonate (200 mg), methanol (3 mL) and water (100 μL)
8. additionwere added to the residue
9. stirringthe mixture was stirred at 50° C. for 2 hr
10. additionThe reaction mixture was diluted with water
11. extractionextracted with ethyl acetate
12. washThe organic layer was washed with water and saturated brine
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationfiltrated
15. concentrationThe filtrate was concentrated under reduced pressure
16. customthe residue was purified by column chromatography (hexane/ethyl acetate=50/50→0/100)
17. customrecrystallized from ethyl acetate