N-bromobutanimide → HCID 178419416, compound

HRID 1851302Notes

Reaction equation

HRID 1851302 reaction equation
[C:1]1([C:7]2[C:8]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:26][CH:25]([C:27]5[N:31]=[C:30]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=6)[NH:29][N:28]=5)[CH2:24]4)=[CH:18][CH:17]=3)=[N:9][C:10]3[N:11]([CH:13]=[CH:14][N:15]=3)[CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:38]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:38][C:13]1[N:11]2[CH:12]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:24][CH:25]([C:27]5[N:31]=[C:30]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=6)[NH:29][N:28]=5)[CH2:26]4)=[CH:18][CH:17]=3)=[N:9][C:10]2=[N:15][CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178420104HCID 178420104, compound

Product 1

HCID 178419416HCID 178419416, compoundYield 11.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

143 mg (0.3 mmol) 6-Phenyl-7-{4-{3-[5-(pyridine-2-yl)-1H-[1,2,4]triazole-3-yl)azetidine-1-ylmethyl]-phenyl}-imidazo[1,2-a]pyrimidine are dissolved in 11.8 mL chloroform. 57.8 mg (0.3 mmol) N-bromosuccinimide are added and the reaction mixture is heated for one hour at reflux. The solvent is evaporated and the residue is purified by chromatography (silicagel, eluents: dichloromethane/methanol). 19.1 mg (10%) pure compound and 75.8 mg (41%) slightly contaminated product are obtained.

Workup

  1. temperaturethe reaction mixture is heated for one hour
  2. temperatureat reflux
  3. customThe solvent is evaporated
  4. customthe residue is purified by chromatography (silicagel, eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-efbce9e9b9434544b4849b4a6ff2c79b
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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