Dipropylamine → (S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-one

HRID 1378082Notes

Reaction equation

HRID 1378082 reaction equation
[CH2:1]([NH:4][CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].Cl[CH2:9][C:10]1[O:14][C:13]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[N:21]4[CH2:30][CH2:31][C@H:20]4[C:19]=23)=[N:12][N:11]=1>CN(C)C=O>[CH2:1]([N:4]([CH2:9][C:10]1[O:14][C:13]([C:15]2[N:16]=[CH:17][N:18]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:22](=[O:29])[N:21]4[CH2:30][CH2:31][C@H:20]4[C:19]=23)=[N:12][N:11]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 53723128(S)-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 53964145(S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.94 ml (73 mmol) of dipropylamine was added to a solution of 1.17 g (3.42 mmol) of (S)-1-(5-chloromethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 10 ml of dimethylformamide, whereupon the mixture was stirred at room temperature for 12 hours. The dimethylformamide was evaporated and the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed twice with methylene chloride and the organic phases were dried with sodium sulfate, filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 95:5) yielded 0.900 g (65%) of (S)-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a]-[1,4]benzodiazepin-9-one as a colourless foam, Rf=0.46 (silica gel, methylene chloride/methanol 95:5).

Workup

  1. customThe dimethylformamide was evaporated
  2. customthe residue was partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed twice with methylene chloride
  4. dry with materialthe organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-86c65fd00cbf4277830396238a3d928f
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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