Ethyl Acetate → 1-{4-[(E)-1-(5-Chloro-6-oxo-1,6-dihydropyridin-2-yl)-2-cyclopentylethenyl]phenyl}urea

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Reaction Steps

A solution of potassium cyanate (41 mg) in water (2 mL) was added to a solution of 6-[(E)-1-(4-aminophenyl)-2-cyclopentylethenyl]-3-chloropyridin-2(1H)-one obtained in Example 1-105(1) (153 mg) in acetic acid (2 mL)-water (1 mL), and the mixture was stirred at room temperature for 30 minutes. Saturated aqueous sodium bicarbonate and ethyl acetate were sequentially added to the reaction solution. The organic layer was separated, washed with saturated aqueous sodium bicarbonate and brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=9:1→8:2). This was powdered with ethyl acetate, and filtration operation gave the title compound as a light yellow powder (37 mg, 21%).

Provenance & Evidence