Dibutylamine → HCID 54498054, compound

HRID 1378121Notes

Reaction equation

HRID 1378121 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].Cl[CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[N:18]=[CH:19][N:20]3[C:26]4[CH:27]=[CH:28][S:29][C:25]=4[C:24](=[O:30])[N:23]4[CH2:31][CH2:32][C@H:22]4[C:21]=23)[N:13]=1>CN(C)C=O>[CH2:1]([N:5]([CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[N:18]=[CH:19][N:20]3[C:26]4[CH:27]=[CH:28][S:29][C:25]=4[C:24](=[O:30])[N:23]4[CH2:31][CH2:32][C@H:22]4[C:21]=23)[N:13]=1)[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 54112781HCID 54112781, compound

Product 1

HCID 54498054HCID 54498054, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.6 ml (3.45 mmol) of dibutylamine was added to a suspension of 400 mg (1.15 mmol) of (S)-1-(5-chloromethyl-1,2,4-oxadiazol-3-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e]-[1,4]diazepin-8-one in 10 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 12 hours. The solution was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous solution was extracted with methylene chloride and the organic phases were dried with magnesium sulfate, filtered and evaporated. The residue was chromatographed (silica gel, methyl acetate/methanol 10:1). There were obtained 425 mg (84%) of (S)-1-(5-dibutylaminomethyl-1,2,4-oxadiazol-3-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.31 (silica gel, methyl acetate/methanol 10:1).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. extractionThe aqueous solution was extracted with methylene chloride
  4. dry with materialthe organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed (silica gel, methyl acetate/methanol 10:1)

Sources & evidence

ORD record
ord-ebc6f3eb24fe40b1bb220279d71f7859
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…