N'-hydroxypentanimidamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g (30 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 50 ml of N,N-dimethylformamide, whereupon the solution is treated with 3.96 g (34 mmol) of valeramidoxime and the mixture is heated to 85° for 3 hours. The reaction mixture is evaporated to dryness. The residue is dissolved in 50 ml of glacial acetic acid and the mixture is stirred at 110° for 2 hours. The reaction mixture is subsequently evaporated and the residue is chromatographed on silica gel while eluting with ethyl acetate. After evaporation of the eluate there is obtained (S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 181°-182°. the mixture is heated to 85° for 3 hours The reaction mixture is evaporated to dryness The residue is dissolved in 50 ml of glacial acetic acid The reaction mixture is subsequently evaporated the residue is chromatographed on silica gel while eluting with ethyl acetate After evaporation of the eluate there

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g (30 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 50 ml of N,N-dimethylformamide, whereupon the solution is treated with 3.96 g (34 mmol) of valeramidoxime and the mixture is heated to 85° for 3 hours. The reaction mixture is evaporated to dryness. The residue is dissolved in 50 ml of glacial acetic acid and the mixture is stirred at 110° for 2 hours. The reaction mixture is subsequently evaporated and the residue is chromatographed on silica gel while eluting with ethyl acetate. After evaporation of the eluate there is obtained (S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 181°-182°. the mixture is heated to 85° for 3 hours The reaction mixture is evaporated to dryness The residue is dissolved in 50 ml of glacial acetic acid The reaction mixture is subsequently evaporated the residue is chromatographed on silica gel while eluting with ethyl acetate After evaporation of the eluate there

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11.0 g (30 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole are dissolved in 50 ml of N,N-dimethylformamide, whereupon the solution is treated with 3.96 g (34 mmol) of valeramidoxime and the mixture is heated to 85° for 3 hours. The reaction mixture is evaporated to dryness. The residue is dissolved in 50 ml of glacial acetic acid and the mixture is stirred at 110° for 2 hours. The reaction mixture is subsequently evaporated and the residue is chromatographed on silica gel while eluting with ethyl acetate. After evaporation of the eluate there is obtained (S)-1-(3-butyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 181°-182°. the mixture is heated to 85° for 3 hours The reaction mixture is evaporated to dryness The residue is dissolved in 50 ml of glacial acetic acid The reaction mixture is subsequently evaporated the residue is chromatographed on silica gel while eluting with ethyl acetate After evaporation of the eluate there