反应详情

To a solution of 3-methylpyridine-2-carboxylic acid (53.5 mg, 0.390 mmol) in tetrahydrofuran (3 mL) were added oxalyl chloride (68.0 μL, 0.780 mmol) and N,N-dimethylformamide (1 drop), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in N,N-dimethylacetamide (3 mL). N-[6-(3-Aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (60.0 mg, 0.195 mmol) was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 15 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 (NH silica gel, ethyl acetate) and recrystallized from ethyl acetate to give the title compound (58.0 mg, 70%) as a white solid.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (3 mL)
3. stirringwith stirring under ice-
4. temperaturecooling
5. stirringthe mixture was stirred at room temperature for 15 hr
6. extractionextracted with ethyl acetate
7. washThe organic layer was washed with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltrated
10. concentrationThe filtrate was concentrated under reduced pressure
11. customthe residue was purified by column chromatography (NH silica gel, ethyl acetate)
12. customrecrystallized from ethyl acetate