Allyl bromide → HCID 53957199, compound

HRID 1378033Notes

Reaction equation

HRID 1378033 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]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N(C(C)C)[CH:28]([CH3:30])[CH3:29])C.[CH2:34](Br)[CH:35]=[CH2:36]>C(Cl)Cl>[CH2:30]([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]=[CH:21][C:16]=4[C:15](=[O:22])[N:14]4[CH2:23][CH2:24][C@H:13]4[C:12]=23)[O:5][N:4]=1)[CH2:36][CH:35]=[CH2:34])[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 54124626HCID 54124626, compound

Product 1

HCID 53957199HCID 53957199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.72 g (14.6 mmol) of crude (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 70 ml of methylene chloride, 6 ml (35 mmol) of N-ethyldiisopropylamine and 3.53 g (29.2 mmol) of allyl bromide were stirred at room temperature for 60 hours. The reaction mixture was evaporated and the residue was chromatographed on 180 g of silica gel while eluting with ethyl acetate. By concentrating the uniform fractions there was obtained (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-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. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on 180 g of silica gel
  3. washwhile eluting with ethyl acetate
  4. concentrationBy concentrating the uniform fractions

Sources & evidence

ORD record
ord-a100dcf490cc425ab88043a9902da48a
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

Loading…