Allyl bromide → HCID 53750833, compound

HRID 1378020Notes

Reaction equation

HRID 1378020 reaction equation
[NH2:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([F:25])([F:24])[F:23])[C:16]=4[C:15](=[O:26])[N:14]4[CH2:27][CH2:28][C@H:13]4[C:12]=23)[N:4]=1.C(N(C(C)C)[CH:32]([CH3:34])[CH3:33])C.[CH2:38](Br)[CH:39]=[CH2:40]>C(Cl)Cl>[CH2:34]([N:1]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:9]=[CH:10][N:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([F:25])([F:24])[F:23])[C:16]=4[C:15](=[O:26])[N:14]4[CH2:27][CH2:28][C@H:13]4[C:12]=23)[N:4]=1)[CH2:40][CH:39]=[CH2:38])[CH:32]=[CH2:33]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 54047026HCID 54047026, compound

Product 1

HCID 53750833HCID 53750833, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g (7.7 mmol) of crude (S)-1-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 50 ml of methylene chloride, 14.2 ml (72 mmol) of N-ethyldiisopropylamine and 5.14 g (3.6 mmol) of allyl bromide were stirred at room temperature overnight and at 40° for 4 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 390 g of silica gel while eluting with ethyl acetate. There were obtained 1.50 g (41%) of (S)-1-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was converted into the dihydrochloride with methanolic hydrochloric acid.

Workup

  1. washThe reaction solution was washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe residue was chromatographed on 390 g of silica gel
  5. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-c0a8778b0509415f84dbb7521eca1b39
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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