反应详情

温度

70 °C

Sodium azide (0.15 g) was added to a solution of 2-{4-chloro-1-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}butyl}-5-(4-fluorophenyl)[1,3,4]oxadiazole (366 mg) in DMSO (10 mL) at room temperature, and the reaction solution was stirred at 70° C. for six hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and a saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. Triphenylphosphine (0.33 g) was added to a mixed solution of the resulting residue in THF (10 mL) and water (0.5 mL) at room temperature, and the reaction solution was stirred at 60° C. for three hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. THF and toluene were added to the residue, and the solution was again concentrated under reduced pressure. A solution of the resulting residue in acetic acid (5 mL) was stirred at 150° C. for 1.5 hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the resulting residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system), solidified with ethyl acetate and hexane and separated by filtration to obtain 188 mg of the title compound. The property values of the compound are as follows.

1. waitThe reaction solution was left
2. temperatureto cool to room temperature
3. customthe organic layer was separated
4. washThe resulting organic layer was washed with a saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTriphenylphosphine (0.33 g) was added to a mixed solution of the resulting residue in THF (10 mL)
8. stirringwater (0.5 mL) at room temperature, and the reaction solution was stirred at 60° C. for three hours
9. waitThe reaction solution was left
10. temperatureto cool to room temperature
11. concentrationconcentrated under reduced pressure
12. additionTHF and toluene were added to the residue
13. concentrationthe solution was again concentrated under reduced pressure
14. stirringA solution of the resulting residue in acetic acid (5 mL) was stirred at 150° C. for 1.5 hours
15. waitThe reaction solution was left
16. temperatureto cool to room temperature
17. concentrationconcentrated under reduced pressure
18. additionA saturated sodium bicarbonate solution was added to the resulting residue
19. extractionfollowed by extraction with chloroform
20. extractionThe resulting extract
21. dry with materialwas dried over magnesium sulfate
22. concentrationconcentrated under reduced pressure
23. customThe residue was purified by silica gel column chromatography (carrier
24. washelution solvent
25. customseparated by filtration