Dipropylamine → HCID 22914574, compound

HRID 1378176Notes

Reaction equation

HRID 1378176 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]=[C:21]([C:22]([F:25])([F:24])[F:23])[C:16]=4[C:15](=[O:26])[N:14]([CH3:27])[CH2:13][C:12]=23)[N:4]=1.[CH2:28]([NH:31][CH2:32][CH2:33][CH3:34])[CH2:29][CH3:30]>CN(C)C=O>[CH2:28]([N:31]([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]=[C:21]([C:22]([F:25])([F:24])[F:23])[C:16]=4[C:15](=[O:26])[N:14]([CH3:27])[CH2:13][C:12]=23)[N:4]=1)[CH2:32][CH2:33][CH3:34])[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 22914583HCID 22914583, compound

Product 1

HCID 22914574HCID 22914574, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.19 g (3 mmol) of 3-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-5-methyl-7-trifluoromethyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one were stirred at room temperature for 5 hours with 1.02 g (10 mmol) of dipropylamine and 15 ml of N,N-dimethylformamide. After evaporating the reaction mixture the residue was dissolved in methylene chloride and the solution was washed with water. By drying the organic phase over magnesium sulfate and evaporating the solvent there were obtained 1.33 g (96%) of 3-(5-dipropylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-7-trifluoromethyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 216°-218°.

Workup

  1. customAfter evaporating the reaction mixture the residue
  2. dissolutionwas dissolved in methylene chloride
  3. washthe solution was washed with water
  4. dry with materialBy drying the organic phase over magnesium sulfate
  5. customevaporating the solvent there

Sources & evidence

ORD record
ord-db7b9451379b4db7bc88c3c9987b3046
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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