N-bromobutanimide → (3-bromo-6-phenyl-7-{4-{3-[5-(pyridine-2-yl)-1H-[1,2,4]triazole-3-yl)-azetidine-1-ylmethyl]-phenyl}-imidazo[1,2-a]pyrimidin-5-yl)-methylamine

HRID 1851306Notes

Reaction equation

HRID 1851306 reaction equation
[CH3:1][NH:2][C:3]1[N:8]2[CH:9]=[CH:10][N:11]=[C:7]2[N:6]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:22][CH:21]([C:23]4[N:27]=[C:26]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=5)[NH:25][N:24]=4)[CH2:20]3)=[CH:14][CH:13]=2)[C:4]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[Br:40]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:40][C:9]1[N:8]2[C:3]([NH:2][CH3:1])=[C:4]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:5]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][N:19]4[CH2:20][CH:21]([C:23]5[N:27]=[C:26]([C:28]6[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=6)[NH:25][N:24]=5)[CH2:22]4)=[CH:16][CH:17]=3)=[N:6][C:7]2=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178482059HCID 178482059, compound

Product 1

HCID 178482057(3-bromo-6-phenyl-7-{4-{3-[5-(pyridine-2-yl)-1H-[1,2,4]triazole-3-yl)-azetidine-1-ylmethyl]-phenyl}-imidazo[1,2-a]pyrimidin-5-yl)-methylamineYield 26.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

50 mg (0.097 mmol) Methyl-(6-phenyl-7-{4-{3-[5-(pyridine-2-yl)-1H-[1,2,4]triazole-3-yl)-azetidine-1-ylmethyl]-phenyl}-imidazo[1,2-a]pyrimidin-5-yl)-amine 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 purified by chromatography (silicagel, eluents: dichloromethane/methanol). 15 mg (24.7%) 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 purified by chromatography (silicagel, eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-fef83ade0bf94f0ead99f94d26c8b390
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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