Ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetate → 7-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,4-dihydropyrazino[2,3-b]pyrazine-2,3-dione

HRID 80537Notes

Reaction equation

HRID 80537 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:16][CH2:17][C:18]2[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=2[Cl:26])[C:5]([NH:8][C:9](=[O:15])[C:10](OCC)=[O:11])=[N:6][CH:7]=1>COCCOCCOC>[Br:1][C:2]1[N:3]=[C:4]2[N:16]([CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=3[Cl:26])[C:10](=[O:11])[C:9](=[O:15])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 86659420Ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetate

Product 1

HCID 866594217-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,4-dihydropyrazino[2,3-b]pyrazine-2,3-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of ethyl ({5-bromo-3-[(2-chloro-3,6-difluorobenzyl)amino]pyrazin-2-yl}amino)(oxo)acetate (1.20 g) in diglyme was heated at 165° C. for 16 hrs. The volatile components were removed on rotavap and then under vacuum. The residue was subjected to a silica gel column chromatography by using CH2Cl2/MeOH (9:1) as eluents, furnishing 7-bromo-1-(2-chloro-3,6-difluorobenzyl)-1,4-dihydropyrazino[2,3-b]pyrazine-2,3-dione in 43% yield (0.46 g).

Workup

  1. customThe volatile components were removed on rotavap

Sources & evidence

ORD record
ord-6a639fe1e52e48289d1e937d752203e4
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Reaction notes

Loading…