Allyl bromide → HCID 22914325, compound

HRID 1378045Notes

Reaction equation

HRID 1378045 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]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1.C(N(C(C)C)[CH:28]([CH3:30])[CH3:29])C.[CH2:34](Br)[CH:35]=[CH2:36]>CN(C)C=O>[CH2:30]([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]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]([CH3:24])[CH2:13][C:12]=23)[N:4]=1)[CH2:36][CH:35]=[CH2:34])[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 22914503HCID 22914503, compound

Product 1

HCID 22914325HCID 22914325, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g (4.4 mmol) of 3-(5-aminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 20 ml of N,N-dimethylformamide, 210 ml (12 mmol) of N-ethyldiisopropylamine and 1.16 g (9.6 mmol) of allyl bromide were stirred at room temperature for 4 hours. The reaction solution was evaporated and the residue was chromatographed on 250 g of silica gel while eluting with ethyl acetate. The uniform fractions were evaporated. There were obtained 1.54 g (82%) of 3-(5-diallylaminomethyl-1,2,4-oxadiazol-3-yl)-7-chloro-5,6-dihydro-5-methyl-4H-imidazo[1,5-a][1,4]benzodiazepin-6-one, which was converted into the hydrochloride of m.p. 126°-130°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was chromatographed on 250 g of silica gel
  3. washwhile eluting with ethyl acetate
  4. customThe uniform fractions were evaporated

Sources & evidence

ORD record
ord-b7f1d786abb7487f9b0a1102980b54fa
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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