Isopropylamine → HCID 22914355, compound

HRID 1378200Notes

Reaction equation

HRID 1378200 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]([NH2:27])([CH3:26])[CH3:25]>CN(C)C=O>[CH:24]([NH: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)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 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 22914355HCID 22914355, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.30 g (10 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 room temperature for 2.5 hours with 3 g (50 mmol) of isopropylamine and 20 ml of N,N-dimethylformamide. After evaporating the solvent the residue was dissolved in methylene chloride and the solution was washed twice with water. The organic solution was dried over magnesium sulfate and concentrated. By recrystallizing the residue from ethyl acetate there were obtained 2.37 g (67%) of 3-(5-isopropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one of m.p. 142°-144°, which was converted into the hydrochloride of m.p. 252°-254°.

Workup

  1. customAfter evaporating the solvent the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed twice with water
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customBy recrystallizing the residue from ethyl acetate

Sources & evidence

ORD record
ord-00d8d9b0469f41f2823a7810a8dc3a94
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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