Ammonia → 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-3-carboxamide
Reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](O)=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:21].C(N1C=CN=C1)([N:24]1C=CN=C1)=O.C(=O)=O.N>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:20])[N:9]([CH3:19])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:24])=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[F:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
19.8 g (0.0639 mol) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid were suspended in 100 ml of N,N-dimethylformamide while gassing with argon and treated portionwise at room temperature with 10.9 g (0.0671 mol) of 1,1'-carbonyldiimidazole. After the CO2 evolution had finished the beige suspension was stirred at 50° for 30 min., cooled and treated dropwise at a temperature below 25° within about 10 min. with 20 ml of 25% ammonia. After stirring for 15 minutes the brownish solution obtained was poured into 600 ml of ice-water. The mixture was stirred at room temperature for 30 min. and filtered, whereupon the crystals were rinsed with a total of 200 ml of water. After drying there were obtained 14.4 g (73%) of 7-chloro-8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamide as beige crystals; m.p. 292°-294°.
Workup
- temperaturecooled
- stirringAfter stirring for 15 minutes the brownish solution
- customobtained
- stirringThe mixture was stirred at room temperature for 30 min.
- filtrationfiltered, whereupon the crystals
- washwere rinsed with a total of 200 ml of water
- customAfter drying there
Sources & evidence
- ORD record
- ord-382b1fb1a1674bc48366984b94fdda4a
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05665718
Reaction notes
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