Allyl bromide → HCID 54032652, compound

HRID 1377999Notes

Reaction equation

HRID 1377999 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]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[O:5][N:4]=1.[CH2:26](Br)[CH:27]=[CH2:28].N12CCCN=C1CC[CH2:33][CH2:32][CH2:31]2>CN(C)C=O>[CH2:26]([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]([Cl:22])[C:16]=4[C:15](=[O:23])[N:14]4[CH2:24][CH2:25][C@H:13]4[C:12]=23)[O:5][N:4]=1)[CH2:33][CH:32]=[CH2:31])[CH:27]=[CH2:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53887943HCID 53887943, compound

Product 1

HCID 54032652HCID 54032652, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.02 g (14 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, 75 ml of N,N-dimethylformamide, 21 g (173.8 mmol) of allyl bromide and 29.4 g (193 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) were stirred at 75° for 60 hours. The solution was concentrated and the residue was purified by chromatography on 350 g of silica gel while eluting with ethyl acetate. There were obtained 1.97 g (35%) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-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. 190°-192°.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by chromatography on 350 g of silica gel
  3. washwhile eluting with ethyl acetate

Sources & evidence

ORD record
ord-823ed888bcc541fe9ef71bdf722b0c21
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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