反应详情

A mixture of N-(3-{[1-(2-amino-2-oxoethyl)-6-{[(4-methylphenyl)sulfonyl]imino}-1,6-dihydropyridin-3-yl]oxy}phenyl)-6-methylpyridine-2-carboxamide (14.6 g, 27.5 mmol), trifluoroacetic anhydride (31 mL) and tetrahydrofuran (300 mL) was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, ethanol (200 mL) and 4M aqueous sodium hydroxide solution (80 mL) were added to the residue, and the mixture was stirred at 60° C. for 24 hr. The reaction solution was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture 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 silica gel column chromatography (NH silica gel, 0%→100% ethyl acetate-hexane) to give the title compound (2.22 g, 22%) as a pale-brown solid.

1. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
2. additionwas added to the residue
3. washThe mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltrated
6. concentrationThe filtrate was concentrated under reduced pressure, ethanol (200 mL) and 4M aqueous sodium hydroxide solution (80 mL)
7. additionwere added to the residue
8. stirringthe mixture was stirred at 60° C. for 24 hr
9. concentrationThe reaction solution was concentrated under reduced pressure, and ethyl acetate
10. additionwas added to the residue
11. washThe mixture was washed with water and saturated brine
12. dry with materialdried over anhydrous magnesium sulfate
13. filtrationfiltrated
14. concentrationThe filtrate was concentrated under reduced pressure
15. customthe residue was purified by silica gel column chromatography (NH silica gel, 0%→100% ethyl acetate-hexane)