反应详情

温度

80 °C

A mixture of 5-chloro-2-[chloro(cyclohexyl)methyl]-3-methyl-1-benzofuran (270 mg) synthesized above, ethyl 3-{[(4-aminophenyl)carbonyl]amino}propanoate (215 mg) synthesized in Example 1(2), sodium iodide (204 mg), sodium carbonate (144 mg) and N,N-dimethylformamide (10 mL) was stirred overnight at 80° C. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane) to give a pale-yellow oil. To a mixture of the obtained oil, tetrahydrofuran (5 mL) and ethanol (5 mL) 1N aqueous sodium hydroxide solution (1.00 mL) was added, and the mixture was stirred at room temperature for 2 hr, and the reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (1.00 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (132 mg, 31%) as a yellow solid.

1. customto quench
2. customthe reaction
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane)
8. customto give a pale-yellow oil
9. additionwas added
10. stirringthe mixture was stirred at room temperature for 2 hr
11. concentrationthe reaction mixture was concentrated under reduced pressure
12. dissolutionThe residue was dissolved in water (10 mL)
13. addition1N hydrochloric acid (1.00 mL) was added at 0° C
14. filtrationThe resulting precipitate was collected by filtration