Hydrochloric Acid → 7-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride

HRID 1378221Notes

Reaction equation

HRID 1378221 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:30])[N:9]([CH3:29])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:31].Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[C:7]2[C:8](=[O:30])[N:9]([CH3:29])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:22]([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:24])[CH3:25])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[F:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22914338HCID 22914338, compound

Product 1

HCID 229143377-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochlorideYield 166.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.82 g (1.84 mmol) of 7-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one was dissolved in 20 ml of hot ethanol and treated at 0° with 0.55 ml (2.02 mmol) of 3.7N ethanolic hydrochloric acid. After stirring at 0° for 30 minutes the solution was totally concentrated. The product was recrystallized from hot acetonitrile/ethyl acetate. There was obtained 0.74 g (83%) of 7-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-8-fluoro-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1) as white crystals; m.p. 206°-210° (dec.).

Workup

  1. concentrationwas totally concentrated
  2. customThe product was recrystallized from hot acetonitrile/ethyl acetate

Sources & evidence

ORD record
ord-2e2f472e7c814243b7ac3f65ef2e40f7
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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