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 1378155Notes

Reaction equation

HRID 1378155 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 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.2 g (180 mmol) of sodium were dissolved in 225 ml of methanol. 13.55 g (195 mmol) of hydroxylamine hydrochloride and 40 g (149 mmol) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile were added and the reaction mixture was stirred at boiling temperature overnight. The suspension was cooled to 5° and suction filtered. The crystals were rinsed with water and dried. There were obtained 38.9 g (87%) of (S)-7-fluoro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime, which was used in the next step without further purification.

Workup

  1. temperatureThe suspension was cooled to 5°
  2. filtrationsuction filtered
  3. washThe crystals were rinsed with water
  4. customdried

Sources & evidence

ORD record
ord-18f4990b72214a3c87612e255dd09db6
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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