1-Bromopropane → HCID 22914420, compound

HRID 1378258Notes

Reaction equation

HRID 1378258 reaction equation
C(N(C(C)C)[CH:4]([CH3:6])[CH3:5])C.[CH2:10](Br)[CH2:11][CH3:12].[NH2:14][CH2:15][C:16]1[O:20][C:19]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]([CH3:35])[CH2:26][C:25]=23)=[N:18][N:17]=1>CN(C)C=O>[CH2:10]([N:14]([CH2:15][C:16]1[O:20][C:19]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][S:33][C:29]=4[C:28](=[O:34])[N:27]([CH3:35])[CH2:26][C:25]=23)=[N:18][N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 22914591HCID 22914591, compound

Product 1

HCID 22914420HCID 22914420, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.48 ml (20 mmol) of N-ethyldiisopropylamine and 1.1 ml (12 mmol) of propyl bromide were added to a solution of 0.632 g (2 mmol) of 3-(5-aminomethyl-1,3,4-oxadiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one in 20 ml of dimethylformamide, whereupon the mixture was stirred at 70° 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, ethyl acetate/methanol 20:1) yielded 0.395 g (49%) of 3-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one as a colourless foam, Rf=0.33 (silica gel, ethyl acetate/methanol 20:1).

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-cb8befee43754f7a99bcedee95cef5c4
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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