Benzoyl Peroxide → 2-Bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

HRID 2231070Notes

Reaction equation

HRID 2231070 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[CH:10]=2)[C:5]2[N:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]=1.[Br:30]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Br:30][CH2:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:25])[C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[CH:10]=2)[C:5]2[N:26]=[CH:27][CH:28]=[CH:29][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 227243002-Methyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 227245262-Bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 26.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The mixture of 2-methyl-4-[3-(3,5-dichlorobenzoylamino) phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (4.4 g), N-bromosuccinimide (2.39 g) and benzoylperoxide in chloroform (40 ml) was refluxed for 3 hours. The mixture was washed with water and extracted by chloroform (80 ml), and evaporated. The crude product was purified by chromatography to obtain 2-bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (1.4 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. washThe mixture was washed with water
  3. extractionextracted by chloroform (80 ml)
  4. customevaporated
  5. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-23495ff00883453989fe4dabc8f7f66d
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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