Diisopropylamine → 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 1378197Notes

Reaction equation

HRID 1378197 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:27][CH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>CN(C)C=O>[CH:24]([N:27]([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:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 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 229145363-(5-diisopropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-oneYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

72 g (212 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 80° for 16 hours in 150 ml (1.06 mol) of diisopropylamine and 300 ml of N,N-dimethylformamide. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was extracted twice with 100 ml of 2N hydrochloric acid. The acidic phase was made alkaline with conc. sodium hydroxide solution and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and evaporated. By chromatography of the residue on silica gel while eluting with ethyl acetate/methanol/acetic acid 95/3/2 and recrystallization from ethanol there were obtained 51.6 g (61%) of 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. 117°-119°.

Workup

  1. customAfter evaporating the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. extractionthe solution was extracted twice with 100 ml of 2N hydrochloric acid
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. washBy chromatography of the residue on silica gel while eluting with ethyl acetate/methanol/acetic acid 95/3/2 and recrystallization from ethanol

Sources & evidence

ORD record
ord-2f27d5efaf7b4bb099f0ac7c59a99225
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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