Hydrochloric Acid → 7-(2-chloro-3,6-difluoro-phenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one

HRID 1512062Notes

Reaction equation

HRID 1512062 reaction equation
CO[C:3]([C:5]1[C:10]([NH:11][C:12](=[O:23])[CH2:13][C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=2[Cl:22])=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].O.Cl>CN(C)C=O>[Cl:22][C:15]1[C:16]([F:21])=[CH:17][CH:18]=[C:19]([F:20])[C:14]=1[C:13]1[C:12](=[O:23])[NH:11][C:10]2=[N:9][CH:8]=[CH:7][N:6]=[C:5]2[C:3]=1[OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 579988233-[2-(2-Chloro-3,6-difluoro-phenyl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester

Product 1

HCID 579988247-(2-chloro-3,6-difluoro-phenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-oneYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[2-(2-Chloro-3,6-difluoro-phenyl)-acetylamino]-pyrazine-2-carboxylic acid methyl ester (4.15 g) (Example 1.1) was heated with potassium carbonate (1.67 g) in N,N-dimethylformamide (50 ml) at 110° C. for 2 hours and then stored at ambient temperature for 16 hours. Water was added and the reaction mixture was acidified with aqueous hydrochloric acid (concentrated). A precipitate formed which was isolated by filtration. The residue was washed successively with water and hexane to produce 7-(2-chloro-3,6-difluoro-phenyl)-8-hydroxy-5H-pyrido[2,3-b]pyrazin-6-one as a brown solid (2.88 g). 1H-NMR (400 MHz, d6-DMSO): 7.34-7.42 (m, 1H), 7.51-7.59 (m, 1H), 8.59 (d, 1H), 8.72 (d, 1H), 12.0 (bs, 1H), 12.4 (s, 1H) ppm.

Workup

  1. customA precipitate formed which
  2. customwas isolated by filtration
  3. washThe residue was washed successively with water and hexane

Sources & evidence

ORD record
ord-d3f33c3d91ec4b41858c9ddb4237d811
Source dataset
uspto-grants-2012_07
Patent number
US08217055B2

Reaction notes

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