1-Bromopropane → HCID 22914226, compound

HRID 1378107Notes

Reaction equation

HRID 1378107 reaction equation
C(N(C(C)C)[CH:4]([CH3:6])[CH3:5])C.Br[CH2:11][CH2:12][CH3:13].[NH2:14][CH2:15][C:16]1[N: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)[O:18][N:17]=1>CN(C)C=O>[CH2:11]([N:14]([CH2:15][C:16]1[N: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)[O:18][N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 22914543HCID 22914543, compound

Product 1

HCID 22914226HCID 22914226, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 ml (23.4 mmol) of N-ethyldiisopropylamine and 1.1 ml (12 mmol) of 1-bromopropane were added to a solution of 0.6 g (1.9 mmol) of 3-(3-aminomethyl-1,2,4-oxadiazol-5-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 and the mixture was stirred at 70° for 1 hour. The reaction solution was subsequently evaporated, whereupon the residue was partitioned between methylene chloride and 2N sodium carbonate solution. The aqueous phase was washed three times with methylene chloride. The organic phases were dried with magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, ethyl acetate/methanol 25:1). There were obtained 440 mg (57%) of 3-(3-dipropylaminomethyl-1,2,4-oxadiazol-5-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=0.34 (silica gel, ethyl acetate/methanol 25:1).

Workup

  1. customThe reaction solution was subsequently evaporated, whereupon the residue
  2. customwas partitioned between methylene chloride and 2N sodium carbonate solution
  3. washThe aqueous phase was washed three times with methylene chloride
  4. dry with materialThe organic phases were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas chromatographed (silica gel, ethyl acetate/methanol 25:1)

Sources & evidence

ORD record
ord-2bc7f1fd86254bb9a93f8ac7af0603dd
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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