反应详情

IPEA (1.2 mL), EDC (0.89 g) and HOBT (0.62 g) were added to a suspension of 5-chloro-2-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}valeric acid trifluoroacetic acid salt (1.30 g) and 4-fluorobenzhydrazide (0.37 g) in DMF (25 mL) at room temperature, and the reaction solution was stirred at room temperature for two hours. A saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer washed with a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. A solution of the resulting residue in phosphorus oxychloride (6 mL) was heated under reflux for three 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) to obtain 376 mg of the title compound. The property value of the compound is as follows.

1. customthe organic layer was separated
2. washThe organic layer washed with a saturated sodium chloride solution
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. temperatureA solution of the resulting residue in phosphorus oxychloride (6 mL) was heated
6. temperatureunder reflux for three hours
7. waitThe reaction solution was left
8. temperatureto cool to room temperature
9. concentrationconcentrated under reduced pressure
10. additionA saturated sodium bicarbonate solution was added to the resulting residue
11. extractionfollowed by extraction with chloroform
12. extractionThe resulting extract
13. dry with materialwas dried over magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)