Allyl bromide → HCID 54533525, compound

HRID 1378003Notes

Reaction equation

HRID 1378003 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([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)[O:5][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[N:7]=[C:6]([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)[O:5][N:4]=1)[CH2:40][CH:39]=[CH2:38])[CH:32]=[CH2:33]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 54132471HCID 54132471, compound

Product 1

HCID 54533525HCID 54533525, compoundYield 191.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g (5.1mmol) of crude (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-trifluoromethyl-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 30 ml of methylene chloride, 6.2 ml (36 mmol) of N-ethyldiisopropylamine and 2.57 g (1.8 mmol) of allyl bromide were stirred at room temperature for 18 hours. The reaction solution was washed three times with water, dried over magnesium sulfate and evaporated. The residue was chromatographed on 300 g of silica gel while eluting with ethyl acetate. There were obtained 1.62 g (67%) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-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 hydrochloride of m.p. 147°-150°.

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 300 g of silica gel
  5. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-a082d542c6bd4a168a6815dc0d214496
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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