Ammonia → (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide

HRID 1378153Notes

Reaction equation

HRID 1378153 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15](O)=[O:16])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][N:8]3[C:7](=[O:20])[C:6]=2[CH:21]=1.C(N1C=CN=C1)([N:24]1C=CN=C1)=O.N.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([NH2:24])=[O:16])=[C:10]3[C@@H:9]3[CH2:18][CH2:19][N:8]3[C:7](=[O:20])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 22828763(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxylic acid

Product 1

HCID 22876619(S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 g (348 mmol) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid were suspended in 600 ml of N,N-dimethylformamide and treated with 64.1 g (395 mmol) of 1,1'-carbonyldiimidazole. After stirring at 50° for 30 minutes 80 ml of 25% ammonia were added dropwise at 13° to 20° and the mixture was stirred for 30 minutes and poured into 21 of water. By suction filtration of the resulting suspension and drying the crystals there were obtained 52.7 g (76%) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide of m.p. 223°-224°.

Workup

  1. additionwere added dropwise at 13° to 20°
  2. filtrationBy suction filtration of the resulting suspension
  3. customdrying the crystals

Sources & evidence

ORD record
ord-988b62287c3d45e49e10a08f11b49faa
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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