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

HRID 1378000Notes

Reaction equation

HRID 1378000 reaction equation
[Na].Cl.[NH2:3][OH:4].[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]3[CH:16]=[N:17][C:18]([C:19]#[N:20])=[C:14]3[C@@H:13]3[CH2:21][CH2:22][N:12]3[C:11](=[O:23])[C:10]=2[CH:24]=1>CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]3[CH:16]=[N:17][C:18]([C:19](=[N:3][OH:4])[NH2:20])=[C:14]3[C@@H:13]3[CH2:21][CH2:22][N:12]3[C:11](=[O:23])[C:10]=2[CH:24]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 22876618(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 54513121(S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto-[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoximeYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.60 g (26 mmol) of sodium was dissolved in 32 ml of methanol. 1.95 g (28.1 mmol) of hydroxylamine hydrochloride and, after 1 hour, 5.77 g (346 mmol) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile were added at room temperature. The suspension was stirred at 70° for 3.5 hours, cooled to 0° during 30 min. and the crystals were filtered off. By drying the crystallizate there were obtained 6.5 g (100%) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime of m.p. 248°-250°.

Workup

  1. temperaturecooled to 0° during 30 min.
  2. filtrationthe crystals were filtered off
  3. customBy drying the crystallizate there

Sources & evidence

ORD record
ord-64c7e4e024554bcca9a1ace56cb5b8da
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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