Pyridine → HCID 54001083, compound

Participants

Reaction Steps

2.38 g (7.85 mmol) of (S)-7-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide were suspended in 15 ml of dioxan and 1.4 ml of pyridine and treated dropwise at a temperature of about 10° with 1.2 ml (8.25 mmol) of trifluoroacetic anhydride. The mixture was stirred at room temperature for 45 min. and a further 0.26 ml of pyridine and 0.11 ml of trifluoroacetic anhydride were added. The reaction mixture was stirred for 30 min. Thereupon, the solvent was removed in a vacuum and the residue was triturated with 30 ml of water. The crude material was chromatographed on 50 g of silica gel (methylene chloride/acetone 9:1). The product was recrystallized from acetonitrile. There were obtained 1.75 g (80%) of (S)-7-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile of m.p. 258°-261°.

Provenance & Evidence