Allyl bromide → HCID 53996798, compound

HRID 1378011Notes

Reaction equation

HRID 1378011 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:37])=[C:34]([O:35][CH3:36])[C:29]=4[C:28](=[O:38])[N:27]4[CH2:39][CH2:40][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:37])=[C:34]([O:35][CH3:36])[C:29]=4[C:28](=[O:38])[N:27]4[CH2:39][CH2:40][C@H: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 54319522HCID 54319522, compound

Product 1

HCID 53996798HCID 53996798, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.1ml (29.8 mmol) of N-ethyldiisopropylamine and 1.46 ml (17.34 mmol) of allyl bromide were added to a solution of 800 mg (2.16 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-8-methoxy-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one in 12 ml of methylene chloride. The reaction solution was stirred at room temperature for 20 hours, subsequently 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 770 mg (79%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-fluoro-8-methoxy-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as a colourless foam, Rf=0.37 (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-b950b64022eb4d5591eed9bc59266a52
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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