N-bromobutanimide → 6-Bromo-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1640688Notes

Reaction equation

HRID 1640688 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[C:10](=[O:11])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:8]([CH3:22])=[CH:7][N:6]=1)=[O:4].[Br:24]N1C(=O)CCC1=O>CN(C=O)C>[Br:24][C:7]1[N:6]=[C:5]([C:3]([N:2]([CH3:23])[CH3:1])=[O:4])[C:10](=[O:11])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[C:8]=1[CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66738834N,N,5-Trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

Product 1

HCID 667390956-Bromo-N,N,5-trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamideYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,5-Trimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide (0.14 g, 0.43 mmol) was dissolved under argon in DMF (2 ml) in a vial. N-Bromosuccinimide (0.089 g, 0.5 mmol) was added. The vial was sealed and stirred for 30 minutes. The crude mixture was purified on preparative HPLC to give 0.100 g (57%) of the title compound as a solid.

Workup

  1. customThe vial was sealed
  2. customThe crude mixture was purified on preparative HPLC

Sources & evidence

ORD record
ord-c56650189cac43a6b2c1ffa91ea4ebc9
Source dataset
uspto-grants-2012_02
Patent number
US08114881B2

Reaction notes

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