Allyl bromide → HCID 54200554, compound

HRID 1378078Notes

Reaction equation

HRID 1378078 reaction equation
C(N(C(C)C)[CH:4]([CH3:6])[CH3:5])C.[CH2:10](Br)[CH:11]=[CH2:12].[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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)=[N:18][N:17]=1>C(Cl)Cl>[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]4[CH2:35][CH2:36][C@H:26]4[C:25]=23)=[N:18][N:17]=1)[CH2:6][CH:4]=[CH2:5])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 22876586HCID 22876586, compound

Product 1

HCID 54200554HCID 54200554, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2 ml (11.5 mmol) of N-ethyldiisopropylamine and 0.97 ml (8 mmol) of allyl bromide were added to a solution of 0.500 g (1.52 mmol) of (S)-1-(5-aminomethyl-1,3,4-oxadiazol-2-yl)-11,11a-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]thieno[3,2-e][1,4]diazepin-8-one in 30 ml of methylene chloride, whereupon the mixture was stirred at 70° for 12 hours. The reaction solution was diluted with methylene chloride and washed with 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 10:1) yielded 0.476 g (77%) of (S)-1-[5-diallylaminomethyl-1,3,4-oxadiazol-2-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=0.36 (silica gel, ethyl acetate/methanol 20:1).

Workup

  1. washwashed with 2N sodium carbonate solution
  2. washThe aqueous phase was washed twice with methylene chloride
  3. dry with materialthe organic phases were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-11cb3cf1de274b6b9b5ae2ac2619113d
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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