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

HRID 1378199Notes

Reaction equation

HRID 1378199 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21]Cl)[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:25]([NH:28][CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:24])[N:9]([CH3:23])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]3[N:20]=[C:19]([CH2:21][N:28]([CH:29]([CH3:31])[CH3:30])[CH:25]([CH3:27])[CH3:26])[O:18][N:17]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 224621917-Chloro-3-(5-chloromethyl-[1,2,4]oxadiazol-3-yl)-5-methyl-4,5-dihydro-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 229145077-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.82 g (5 mmol) of 7-chloro-3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at 80° overnight with 3 ml (21.3 mmol) of diisopropylamine and 20 ml of N,N-dimethylformamide. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol/ammonia 15/15/5/0.5 there were obtained 1.41 g (66%) of 7-chloro-3-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 58°-63°, which was converted into the hydrochloride of m.p. 230°-231°.

Workup

  1. customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
  2. washwhile eluting with cyclohexane/ether/isopropanol/ammonia 15/15/5/0.5 there

Sources & evidence

ORD record
ord-e003ac0674b949eb8f5075a2f8158316
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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