Dibutylamine → HCID 53697728, compound

HRID 1378227Notes

Reaction equation

HRID 1378227 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]4[CH2:23][CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1.[CH2:26]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29]>CN(C)C=O>[CH2:26]([N:30]([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]4[CH2:23][CH2:24][CH2:25][C@H:13]4[C:12]=23)[N:4]=1)[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 53721246HCID 53721246, compound

Product 1

HCID 53697728HCID 53697728, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 711 mg (2.0 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one in 10 ml of N,N-dimethylformamide was treated with 1.0 ml (6.0 mmol) of dibutylamine and stirred at room temperature under argon for 3 hrs. The solution was evaporated, the residue was triturated in 10 ml of water and the crystals were filtered off under suction. The crude product was dissolved in methylene chloride, the solution was dried with sodium sulfate, whereupon it was chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1, then 4:1). There was obtained 0.73 g of (S)-1-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted in 10 ml of acetonitrile with ethereal hydrochloric acid into the hydrochloride. By crystallization from hot ethyl acetate there was obtained 0.75 g (77%) of (S)-1-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one hydrochloride (1:1) of m.p. 115°-123° (dec.).

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated in 10 ml of water
  3. filtrationthe crystals were filtered off under suction
  4. dissolutionThe crude product was dissolved in methylene chloride
  5. dry with materialthe solution was dried with sodium sulfate, whereupon it
  6. customwas chromatographed on 30 g of silica gel (methylene chloride/acetone 9:1

Sources & evidence

ORD record
ord-980f1613941141ce895a301ff58f2c74
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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