Hydrochloric Acid → HCID 22181086, compound

Participants

Reaction Steps

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-(piperidin-4-yloxy)phenyl]ethanesulfonamide dihydrochloride (0.68 g) obtained in example 100(a) in ethanol (15 ml) were added successively 5-methoxy-3,4-dihydro-2H-pyrrole (0.36 g), which was prepared from 2-pyrrolidinone according to the method described in Org. Prep. Proced. Int., 24, 147 (1992), and triethylamine (0.85 ml) at room temperature and the resulting mixture was allowed to stand at room temperature overnight. At the end of this time, to the reaction mixture were furthermore added successively 5-methoxy-3,4-dihydro-2H-pyrrole (0.19 g) and triethylamine (0.34 ml) at room temperature, and the resulting mixture was stirred at room temperature for 5 hours and then evaporated in vacuo. Subsequently, to the residue obtained were successively added ethanol (10 ml) and a 4N solution of hydrogen chloride in dioxane (4 ml), and the resulting mixture was evaporated in vacuo. The residue obtained was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: 10% acetonitrile/water). To the amorphous solid obtained was added 1N hydrochloric acid (8 ml) and the resulting mixture was evaporated to dryness in vacuo. The residue obtained was dissolved in water and then lyophilized to afford the title compound (0.56 g, yield: 73%) as a pale brown amorphous solid.

Provenance & Evidence