N-bromobutanimide → HCID 178424647, compound

HRID 1851304Notes

Reaction equation

HRID 1851304 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][N:17]4[CH2:20][CH:19]([C:21]5[N:25]=[C:24]([C:26]6[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=6)[NH:23][N:22]=5)[CH2:18]4)=[CH:12][CH:11]=3)[C:7]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:6][N:5]2[CH:39]=1.[Br:40]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:40][C:39]1[N:5]2[CH:6]=[C:7]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][N:17]4[CH2:20][CH:19]([C:21]5[N:25]=[C:24]([C:26]6[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=6)[NH:23][N:22]=5)[CH2:18]4)=[CH:12][CH:11]=3)=[N:9][C:4]2=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178424649HCID 178424649, compound

Product 1

HCID 178424647HCID 178424647, compoundYield 32.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

50 mg (0.098 mmol) 2-Methyl-7-{4-{3-[5-(6-methylpyridine-2-yl)-1H-[1,2,4]triazole-3-yl)-azetidine-1-ylmethyl]-phenyl}-6-phenyl-imidazo[1,2-a]pyrimidine are dissolved in 3.9 mL chloroform. 19.1 mg (0.11 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 (31.5%) of the desired compound 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-cad631b7660e4e08a739e7f6003abfd6
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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