Acetonitrile → N-[3-[3-(Acetylamino)(imino)methylphenyl]-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide

Participants

Reaction Steps

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide dihydrochloride (0.29 g) obtained in example 99(b) in a mixture of dichloromethane (3 ml) and acetonitrile (3 ml) were added successively 4-nitrophenyl acetate (0.09 g) and triethylamine (0.26 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature for 4 hours. After stirring, to the reaction mixture was added dichloromethane, and the organic layer was washed successively with a 0.5N aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (50:0˜47:3). The solid obtained was dissolved in water and then lyophilized to afford the title compound (0.16 g, yield: 58%) as a pale yellow amorphous solid.

Provenance & Evidence