Allyl bromide → HCID 53796219, compound

HRID 1378064Notes

Reaction equation

HRID 1378064 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][CH2:26][C@H:13]4[C:12]=23)[O:5][N:4]=1.C(N(C(C)C)[CH:30]([CH3:32])[CH3:31])C.[CH2:36](Br)[CH:37]=[CH2:38]>CN(C)C=O>[CH2:32]([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][CH2:26][C@H:13]4[C:12]=23)[O:5][N:4]=1)[CH2:38][CH:37]=[CH2:36])[CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 22876576HCID 22876576, compound

Product 1

HCID 53796219HCID 53796219, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g (5.95 mmol) of (S)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, 30 ml of N,N-dimethylformamide, 3.1 ml (17.8 mmol) of N-ethyldiisopropylamine and 1.1 ml (13.1 mmol) of allyl bromide were stirred at room temperature for 1.5 hours. The reaction solution was chromatographed on 250 g of silica gel while eluting with methylene chloride/ethyl acetate 7/3. There were obtained 2 g (81%) of (S)-1-(3-diallylaminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one, which was converted into the hydrochloride of m.p. 175°-177°.

Workup

  1. customThe reaction solution was chromatographed on 250 g of silica gel
  2. washwhile eluting with methylene chloride/ethyl acetate 7/3

Sources & evidence

ORD record
ord-2ab4798cf36a4ab9b27c23e3746b0af6
Source dataset
uspto-grants-1997_09
Patent number
US05665718

Reaction notes

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