Acetic Acid → N-(4-dipropylamino-butyl)-4-{[(1-methyl-1H-imidazol-2-ylmethyl)-(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}-benzamide

Participants

Reaction Steps

The compound (782 mg) obtained in Example 20-3 was dissolved in anhydrous methanol (12 ml) and then added with sodium cyanoborohydride (380 mg) and acetic acid (1.5 ml). Then, the solution was added with a methanol solution (2.0 ml) containing the compound (289 mg) obtained in Example 20-4 at −10° C. and then stirred at room temperature for 12 hours under a nitrogen atmosphere. After completion of the reaction, water was added thereto to stop the reaction. The solvent was distilled off under reduced pressure and chloroform and a 1 mol/l sodium hydroxide aqueous solution were added to the residue to make the pH of the aqueous layer about 10, followed by extraction of the aqueous layer with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The resultant was then concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate) and then treated with hydrochloric acid, thereby obtaining a hydrochloride (316 mg) of the subject compound as a white solid.

Provenance & Evidence