HCID 18680797, compound → HCID 18680884, compound

Participants

Reaction Steps

Thirty milliliters of methanol and 0.20 g of 5% palladium on carbon were added to 2.32 g of a mixture of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]-benzimidazole, and the mixture was stirred in a hydrogen atmosphere at room temperature until the starting material disappeared. The solid material was separated through filtration, and the filtrate was concentrated. The resulting residue was purified through medium-pressure silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 85:15) to separate 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole. Each of these compounds was crystallized from a mixed solvent of chloroform and diethyl ether. The crystals were separated through filtration, and were dried to give 0.354 g of 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]-benzimidazole (261) and 0.330 g of 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (262).

Provenance & Evidence