Ammonia → HCID 53911072, compound

Participants

Reaction Steps

6.1 g (37.9 mmol) of 1,1'-carbonyldiimidazole were added portionwise to a suspension of 11 g (34.5 mmol) of (S)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylic acid in 80 ml of dimethylformamide. The resulting pale brown solution was heated to 50° for 45 minutes. The solution was subsequently cooled to room temperature and 12 ml of aqueous ammonia solution were added dropwise. After stirring for a further 30 minutes the reaction mixture was poured into 150 ml of ice-water and extracted seven times with methylene chloride. Drying of the organic phases with sodium sulfate, filtration and evaporation yielded a colourless residue which was triturated with methylene chloride. After drying in a high vacuum there were obtained 9.8 g of (S)-7,8-difluoro-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide m.p. 221°-224°.

Provenance & Evidence