Hydroxyamine hydrochloride → (S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime

HRID 1377991Notes

Reaction equation

HRID 1377991 reaction equation
[Na].Cl.[NH2:3][OH:4].[Cl:5][C:6]1[C:11]2[C:12](=[O:24])[N:13]3[CH2:23][CH2:22][C@H:14]3[C:15]3[N:16]([CH:17]=[N:18][C:19]=3[C:20]#[N:21])[C:10]=2[CH:9]=[CH:8][C:7]=1[F:25]>CO>[Cl:5][C:6]1[C:11]2[C:12](=[O:24])[N:13]3[CH2:23][CH2:22][C@H:14]3[C:15]3[N:16]([CH:17]=[N:18][C:19]=3[C:20](=[N:3][OH:4])[NH2:21])[C:10]=2[CH:9]=[CH:8][C:7]=1[F:25]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 54499997(S)-8-chloro-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 54002434(S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoximeYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.1 g (134.8 mmol) of sodium were dissolved in 140 ml of methanol. 10 g (145 mmol) of hydroxylamine hydrochloride and 28.6 g (94.5 mmol) of (S)-8-chloro-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carbonitrile were added in succession at room temperature. The suspension was stirred at room temperature overnight, cooled to 0° during 30 min., the crystals were filtered off, suspended in 50 ml of water and filtered off. The methanol solution was concentrated, whereupon the residue was suspended in 30 ml of water and the crystals were filtered off. By drying the combined crystallizate there were obtained 30.94 g (97%) of (S)-8-chloro-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. 236°-238°.

Workup

  1. temperaturecooled to 0° during 30 min.
  2. filtrationthe crystals were filtered off
  3. filtrationfiltered off
  4. concentrationThe methanol solution was concentrated, whereupon the residue
  5. filtrationthe crystals were filtered off
  6. customBy drying the combined crystallizate there

Sources & evidence

ORD record
ord-7f53eb4bcb4040e482db0fb134e8f286
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…