N-bromobutanimide → HCID 178424637, compound

HRID 1851300Notes

Reaction equation

HRID 1851300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:19][CH:18]=3)=[N:10][C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[Br:42]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:42][C:14]1[N:12]2[CH:13]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]([C:17]3[CH:18]=[CH:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][CH:27]([C:30]5[N:34]=[C:33]([C:35]6[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[N:36]=6)[NH:32][N:31]=5)[CH2:26][CH2:25]4)=[CH:21][CH:22]=3)=[N:10][C:11]2=[N:16][CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178424639HCID 178424639, compound

Product 1

HCID 178424637HCID 178424637, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

133 mg (0.24 mmol) 6-(4-fluorophenyl)-7-(4-{4-[5-(6-methylpyridine-2-yl)-1H-[1,2,4]triazole-3-yl]-piperidine-1-ylmethyl}-phenyl)-imidazo[1,2-a]pyrimidine are dissolved in 2.5 mL chloroform. After addition of 65.2 mg (0.37 mmol) N-bromosuccinimide the reaction mixture is heated for three hours at reflux. The solvent is evaporated and the residue purified by chromatography on silicagel (eluents: dichloromethane/methanol) yielding 97.5 mg (60.8%) of the desired product.

Workup

  1. temperatureis heated for three hours
  2. temperatureat reflux
  3. customThe solvent is evaporated
  4. customthe residue purified by chromatography on silicagel (eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-cc591cc0131549caad720a3f4f5a6bd4
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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