反应详情

温度

40 °C

A mixture of hydroxylammonium chloride (0.58 g), sodium hydrogen carbonate (0.93 g) and dimethyl sulfoxide (10 mL) was stirred at 40° C. for 30 min, 2-[(trans-4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexyl)oxy]propanamide (0.3 g) was added, and the mixture was stirred at 90° C. for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (10 mL). N,N′-Carbonyldiimidazole (0.11 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.092 mL) were added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (10 mL), pyridine (0.18 mL) and trifluoroacetic acid anhydride (0.15 mL) were added at 0° C., and the mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as colorless crystals (0.15 g, 47%).

1. stirringthe mixture was stirred at 90° C. for 16 hr
2. washwashed with water
3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
4. customThe solvent was evaporated under reduced pressure
5. dissolutionthe residue was dissolved in tetrahydrofuran (10 mL)
6. additionN,N′-Carbonyldiimidazole (0.11 g) and then 1,8-diazabicyclo[5.4.0]undec-7-ene (0.092 mL) were added
7. stirringthe mixture was stirred at room temperature for 2 hr
8. additionThe reaction mixture was diluted with ethyl acetate
9. washwashed with saturated aqueous potassium hydrogensulfate solution
10. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. dissolutionThe obtained residue was dissolved in tetrahydrofuran (10 mL)
13. additionpyridine (0.18 mL) and trifluoroacetic acid anhydride (0.15 mL) were added at 0° C.
14. stirringthe mixture was stirred for 30 min
15. additionThe reaction mixture was diluted with ethyl acetate
16. washwashed with water
17. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
18. customThe solvent was evaporated under reduced pressure
19. customthe residue was purified by silica gel column chromatography