5-Aminobenzimidazole → HCID 178424603, compound

Participants

Reaction Conditions

Reaction Steps

The compound was synthesized as hydrochloride salt by the following procedure. 4-Nitrophenyl chloroformate (0.564 g, 3.5 mmol) was dissolved CH2Cl2, cooled down to 0° C. and 5-aminobenzimidazole (0.466 g, 3.5 mmol) was added slowly. The mixture was kept at 0° C. for 30 min and then the mixture was allowed to adapt ambient temperature. The mixture was stirred at ambient temperature for 2 h. The resulted solid was withdrawn by suction, dried and taken up in a small amount of DMF. To the solution aminomethyl-(4-chloro-3-methylphenyl)ketone (0.774, 3.5 mmol) and TEA (1.46 ml, 10.5 mmol) was added. The mixture was kept at 40° C. for 2 h. The solvent was removed and purified by means of preparative HPLC. The remains were re-dissolved in MeOH and a small amount of HCl was added (1-2%). The solution was subjected to hydrogenation (PdC, 10% on charcoal, 4 bar, 60° C.) for 4 h. The catalyst was removed by filtration through a pad of CELITE® and the solvent was removed and purified by means of preparative HPLC.

Provenance & Evidence