p-Toluenesulfonic acid → HCID 23145188、化合物

HRID 13333

反応式

HRID 13333 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 23145188HCID 23145188、化合物

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c87dc0f010dc41a69867e6328807e9df
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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