Dimethylformamide → N-(4-fluorophenyl)-N-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}acrylamide

TEA (0.07 mL) was added to a suspension of (4-fluorophenyl)-{5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazol-2-yl}amine synthesized in Example 162 (100 mg) in methylene chloride (3 mL) and THF (2 mL) at room temperature. Acrylic acid chloride (0.03 mL) was added to the reaction solution at 0° C., and the reaction solution was stirred at room temperature for two hours. TEA (0.08 mL) and acrylic acid chloride (0.04 mL) were added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for two hours. Further, DMF (0.5 mL), acetonitrile (0.5 mL), DMAP (2 mg), TEA (0.08 mL) and acrylic acid chloride (0.04 mL) were added and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure. Ethyl acetate and a saturated sodium bicarbonate solution were added to the residue, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 22 mg of the title compound. The property value of the compound is as follows.

1. stirringthe reaction solution was stirred at room temperature for two hours
2. stirringthe reaction solution was stirred at room temperature for 12 hours
3. concentrationThe reaction solution was concentrated under reduced pressure
4. additionEthyl acetate and a saturated sodium bicarbonate solution were added to the residue
5. customthe organic layer was separated
6. dry with materialThe resulting organic layer was dried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (
9. washelution solvent

ORD record

ord-62ae058c4deb477b82de7b36c7a69a60

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935815B2