反应详情

To a mixture of methyl 4-{[cyclohexyl(3-methylthieno[3,2-b]pyridin-2-yl)methyl]amino}benzoate (1.31 g) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the mixture was stirred overnight with heating under reflux. 1N Aqueous sodium hydroxide solution (5 mL) was additionally added, and the mixture was further stirred with heating under reflux for 7 hr, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (15 mL) was added at 0° C. The resulting precipitate was collected by filtration, and the obtained brown solid was dissolved in ethyl acetate. The solution was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (804 mg, 64%) as a brown solid.

1. temperaturewith heating
2. temperatureunder reflux
3. stirringthe mixture was further stirred
4. temperaturewith heating
5. temperatureunder reflux for 7 hr
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in water (20 mL)
8. addition1N hydrochloric acid (15 mL) was added at 0° C
9. filtrationThe resulting precipitate was collected by filtration
10. dissolutionthe obtained brown solid was dissolved in ethyl acetate
11. washThe solution was washed with saturated brine
12. dry with materialdried over magnesium sulfate
13. concentrationconcentrated under reduced pressure
14. washThe residue was washed with diisopropyl ether