Dimethylformamide → HCID 53739287, compound

Participants

Reaction Steps

13.46 g (50 mmol) of (S)-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acid were dissolved in 40 ml of N,N-dimethylformamide, treated portionwise with 10 g (61.7 mmol) of 1,1'-carbonyldiimidazole and stirred at 55° for 30 min. After adding 12.06 g (55 mmol) of phthaloylglycine amidoxime the mixture was stirred at 85 °for 2 hours. 10 ml of trifluoroacetic acid were added and the mixture was stirred at 85 °overnight. The reaction mixture was cooled to 10 °and the crystals were filtered off. After recrystallization from methanol there were obtained 9.16 g (40%) of (S)-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepin-9-one of m.p. 290°-292°.

Provenance & Evidence