Allyl bromide → HCID 54226836, compound

HRID 1378035Notes

Reaction equation

HRID 1378035 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][N:19]=[C:18]([C:21]2[N:22]=[CH:23][N:24]3[C:30]4[CH:31]=[CH:32][C:33]([F:36])=[C:34]([F:35])[C:29]=4[C:28](=[O:37])[N:27]4[CH2:38][CH2:39][C@H:26]4[C:25]=23)[N:17]=1>C(Cl)Cl>[CH2:10]([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][C:33]([F:36])=[C:34]([F:35])[C:29]=4[C:28](=[O:37])[N:27]4[CH2:38][CH2:39][CH:26]4[C:25]=23)[N:17]=1)[CH2:6][CH:4]=[CH2:5])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 22876585(S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Product 1

HCID 54226836HCID 54226836, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.3 ml (13.5 mmol) of N-ethyldiisopropylamine and 0.66 ml (7.8 mmol) of allyl bromide were added to a solution of 700 mg (1.95 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 40 ml of methylene chloride and the mixture was stirred at room temperature for 20 hours. The reaction solution was diluted with methylene chloride and washed three times with water. The organic phases were dried over magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 400 mg (46%) of S)-1-[5-(diallylaminomethyl)-1,2,4-oxadiazol-3-yl]-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as a colourless foam, Rf=0.17 (silica gel, methylene chloride/methanol 19:1).

Workup

  1. washwashed three times with water
  2. dry with materialThe organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas chromatographed (silica gel, methylene chloride/methanol 19:1)

Sources & evidence

ORD record
ord-ecfd39a27c7547d89b71a84614f00437
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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