3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide → 1-(2-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-1H-imidazol-5-yl)-2-methylpropan-1-one

Participants

Reaction Steps

To a solution (40 mL) of 3-cyclopentyl-N-(5-isopropylisoxazol-4-yl)-2-[4-(methylsulfonyl)phenyl]propanamide (2.50 g) in ethanol was added 10% palladium carbon (containing 50% water, 0.500 g) and the mixture was stirred under hydrogen atmosphere (5 atm) for 4 hr. The reaction mixture was filtered to remove the catalyst, sodium hydroxide (0.261 g) was added to the filtrate, and the mixture was heated under reflux for 1 hr. To the reaction mixture was added ammonium chloride (0.430 g), and the mixture was cooled to room temperature, and stirred at room temperature for 16 hr. The reaction solution was concentrated, the obtained residue was suspended in acetone, and the suspension was filtered to remove insoluble materials. The filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=50:50-100:0, volume ratio), and recrystallized from ethyl acetate-hexane to give the title compound (1.20 g, yield 50%) as colorless crystals. melting point 171-172° C.

Provenance & Evidence