1-Bromopropane → HCID 54187179, compound

HRID 1378075Notes

Reaction equation

HRID 1378075 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[O:20][N:19]=[C:18]([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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[N:17]=1>CN(C)C=O>[CH2:11]([N:14]([CH2:15][C:16]1[O:20][N:19]=[C:18]([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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)[N:17]=1)[CH2:5][CH2:4][CH3:6])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 53713947HCID 53713947, compound

Product 1

HCID 54187179HCID 54187179, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.74 ml of N-ethyldiisopropylamine and 0.55 ml (6 mmol) of 1-bromopropane were added to a solution of 0.500 g (1.52 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-I 1,11a-dihydro-8H, 10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 15 ml of dimethylformamide and 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 extracted 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 0.350 g (55%) of (S)-1-(5-dipropylaminomethyl-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=0.44 (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. extractionThe aqueous phase was extracted twice with methylene chloride
  4. dry with materialthe organic phases were dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a781d4e29af540d696c2b731de1446c4
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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