Allyl bromide → HCID 53987453, compound

HRID 1378063Notes

Reaction equation

HRID 1378063 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][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:36])=[C:34]([F:35])[C:29]=4[C:28](=[O:37])[N:27]4[CH2:38][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 22876584HCID 22876584, compound

Product 1

HCID 53987453HCID 53987453, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.1 ml (10.5 mmol) of N-ethyldiisopropylamine and 0.6 ml (7 mmol) of allyl bromide were added to a solution of 650 mg (1.76 mmol) of (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7,8-difluoro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][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 subsequently diluted with methylene chloride and washed three times with water. The organic phases were dried with magnesium sulfate, filtered and evaporated. The residue obtained was chromatographed twice (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:0.1). There were obtained 625 mg (78%) of (S)-1-[5-(diallylaminomethyl)-1,2,4-oxadiazol-3-yl]-7,8-difluoro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c]-[1,4]benzodiazepin-9-one as a colourless foam, Rf=0.45 (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:0.1).

Workup

  1. washwashed three times with water
  2. dry with materialThe organic phases were dried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customwas chromatographed twice (silica gel, methylene chloride/methanol/aqueous ammonia 140:10:0.1)

Sources & evidence

ORD record
ord-6882aee56bd346c5956045cdfb412cc7
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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