Hydrochloric Acid → HCID 178522526, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (3RS)-1,3-dihydro-3-(2-indolylcarbonyl-amino) -5-phenyl-2H-1,4-benzodiazepine-2-one (800 mg), 1-trityl-4-chloromethylimidazole hydrochloride (790 mg) and N,N-dimethylformamide (16 ml) was added sodium hydride (62 % suspension in mineral oil, 168 mg) under stirring and cooling at 0° C. in an ice-bath. The mixture was stirred for 30 minutes at 0° to 5° C. and heated at 70° to 80° C. for 3.0 hours. To the cooled reaction mixture were added acetic acid (2.0 ml) and 6N hydrochloric acid (5 ml). The mixture was stirred for 1.0 hour at 60° C. The cooled reaction mixture was poured into a mixture of ethyl acetate (100 ml) and water (100 ml) under stirring. The organic layer was separated, washed with water three times, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with an eluent of a mixture of chloroform and methanol (20:1) to give (3RS)-1,3-dihydro-3-(2-indolylcarbonylamino) -1-(4-imidazolylmethyl)-5-phenyl-2H-1,4-benzodiazepine-2-one (306.0 mg).

Provenance & Evidence