p-Toluenesulfonic acid → HCID 23145188, compound

HRID 13333

Reaction equation

HRID 13333 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]1[C:22](F)=[C:21]([O:24][C:25]2[CH:26]=[N:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=2)[CH:20]=[C:19]([N+:35]([O-])=O)[C:18]=1[NH:38][C:39]([C:41]1[CH:46]=[N:45][CH:44]=[CH:43][N:42]=1)=O.O.O.[Sn](Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:22]1[C:21]([O:24][C:25]2[CH:26]=[N:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=2)=[CH:20][C:19]2[NH:35][C:39]([C:41]3[CH:46]=[N:45][CH:44]=[CH:43][N:42]=3)=[N:38][C:18]=2[C:17]=1[F:16]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 943922,6-DifluorophenolHCID 23145537N-(2,3-difluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-6-nitro-phenyl)pyrazinecarboxamide

Product 1

HCID 23145188HCID 23145188, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

8 mg of 2,6-difluorophenol and 8 mg of potassium carbonate were added to an N-methylpyrrolidinone (0.5 ml) solution of 8.6 mg of N-(2,3-difluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-6-nitro-phenyl)pyrazinecarboxamide, and the reaction liquid was stirred at 90° C. for 15 minutes. 75 mg of tin(II) chloride dihydrate was added to it, and the reaction liquid was stirred overnight at 90° C. Further, 3 mg of p-toluenesulfonic acid was added to it, and the reaction liquid was stirred at 90° C. for 2 hours. The deposit was taken out through filtration, and purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a brown solid.

Workup

  1. customthe reaction liquid
  2. customthe reaction liquid
  3. stirringwas stirred overnight at 90° C
  4. customthe reaction liquid
  5. stirringwas stirred at 90° C. for 2 hours
  6. filtrationThe deposit was taken out through filtration
  7. custompurified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  8. additionThe solvent of the resulting fraction was diluted with ethyl acetate
  9. washwashed with aqueous saturated sodium bicarbonate
  10. dry with materialdried with anhydrous sodium sulfate
  11. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-c87dc0f010dc41a69867e6328807e9df
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Linked notes

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