DI-Sec-butylamine → 3-(5-di-sec.-butylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

HRID 1378198Notes

Reaction equation

HRID 1378198 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[N:4]=1.[CH:24]([NH:28][CH:29]([CH2:31][CH3:32])[CH3:30])([CH2:26][CH3:27])[CH3:25]>CN(C)C=O>[CH:24]([N:28]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]([CH3:23])[CH2:13][C:12]=23)[N:4]=1)[CH:29]([CH2:31][CH3:32])[CH3:30])([CH2:26][CH3:27])[CH3:25]

Participants

4

Reactant 2

HCID 12277DI-Sec-butylamineHCID 229143143-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 229143413-(5-di-sec.-butylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-oneYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.65 g (5 mmol) of 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 75° for 24 hours in 3 ml (17.5 mmol) of di-sec.-butylamine and 25 ml of N,N-dimethylformamide. By evaporation of the reaction mixture and chromatography of the residue on silica gel while eluting with methylene chloride/methanol 19/1 and crystallization from ethyl acetate there were obtained 1.23 g (58%) of 3-(5-di-sec.-butylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]-benzodiazepin-6-one of m.p. 155°-157°, which was converted into the hydrochloride of m.p. 133°-140°.

Workup

  1. customBy evaporation of the reaction mixture and chromatography of the residue on silica gel
  2. washwhile eluting with methylene chloride/methanol 19/1 and crystallization from ethyl acetate

Sources & evidence

ORD record
ord-18a2187c5e8e4c9789d1faeab7e4a4ba
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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