Dibutylamine → HCID 22914563, compound

HRID 1378232Notes

Reaction equation

HRID 1378232 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20]Cl)[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1.[CH2:25]([NH:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]4[N:19]=[C:18]([CH2:20][N:29]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][CH2:26][CH2:27][CH3:28])[O:17][N:16]=4)=[C:10]3[CH2:9][N:8]([CH3:22])[C:7](=[O:23])[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 22914400HCID 22914400, compound

Product 1

HCID 22914563HCID 22914563, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 278 mg (0.76 mmol) of 8-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 in 5 ml of N,N-dimethylformamide was treated with 0.39 ml (2.3 mmol) of dibutylamine and stirred at room temperature under argon for 1.5 hrs. The solution was evaporated, the residue was dissolved in 20 ml of methylene chloride and the solution was washed three times with water. The organic phase was dried with sodium sulfate, filtered and evaporated. The crude product was chromatographed on 20 g of silica gel (methylene chloride/acetone 4:1). There were obtained 250 mg of 8-chloro-3-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted with ethereal hydrochloric acid into the hydrochloride. By crystallization from acetonitrile there were obtained 151 mg (39%) of 8-chloro-1-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one hydrochloride (1:1.3) of m.p. 165°-175° (dec.).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in 20 ml of methylene chloride
  3. washthe solution was washed three times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed on 20 g of silica gel (methylene chloride/acetone 4:1)

Sources & evidence

ORD record
ord-0de9e082a4b84603a5e11280b8f0ccfc
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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