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

HRID 1378154Notes

Reaction equation

HRID 1378154 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]([NH2:17])=O)=[C:10]3[C@@H:9]3[CH2:18][CH2:19][N:8]3[C:7](=[O:20])[C:6]=2[CH:21]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]#[N:17])=[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 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 22876619(S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 22876618(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrileYield 64.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

75.6 g (264 mmol) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carboxamide were suspended in 340 ml of dioxan and 45 ml of pyridine and treated dropwise at about 7° with (323 mmol) of trifluoroacetic anhydride. The reaction mixture was stirred at room temperature overnight and poured into 2 l of water. By suction filtration of the resulting suspension and drying the crystals there were obtained 45.65 g (64%) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]-benzodiazepine-1-carbonitrile, which was used in the next step without further purification.

Workup

  1. filtrationBy suction filtration of the resulting suspension
  2. customdrying the crystals

Sources & evidence

ORD record
ord-98f195b08684441a8c1349cb09ac8159
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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