Trimethyl orthoformate → N-(4-dipropylaminomethyl-phenyl)-4-{[(1-methylimidazol-2-ylmethyl)-amino]methyl}benzamide

Participants

Reaction Steps

The compound (389 mg) obtained in Example 15-4 was dissolved in anhydrous methanol (10 ml) and then added with trimethyl orthoformate (188 μl) and 2-imidazole carboxaldehyde (139 mg). The whole was stirred overnight at room temperature under a nitrogen atmosphere. Then, sodium borohydride (43.4 mg) was added thereto in an ice bath and the whole was stirred at room temperature for 2.5 hours. After completion of the reaction, distilled water was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (346 mg) as a yellow solid.

Provenance & Evidence