Cesium carbonate → HCID 23145656, Verbindung

HRID 13374

Reaktionsgleichung

Reaktionsgleichung von HRID 13374
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:17]1[C:18]([O:35][C:36]2[CH:37]=[N:38][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][CH:41]=2)=[CH:19][C:20]([N+:32]([O-])=O)=[C:21]([NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=O)[CH:22]=1.O.O.[Sn](Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][C:17]1[C:18]([O:35][C:36]2[CH:37]=[N:38][C:39]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:40][CH:41]=2)=[CH:19][C:20]2[NH:32][C:24]([C:26]3[CH:31]=[N:30][CH:29]=[CH:28][N:27]=3)=[N:23][C:21]=2[CH:22]=1

Komponenten

8

Edukt 5

HCID 10796Cesium carbonateHCID 61436Stannous chloride dihydrateHCID 949522,5-DifluorophenolHCID 516892Sodium BicarbonateHCID 86619212Pyrazine-2-carboxylic acid (5-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenyl)-amide

Produkt 1

HCID 23145656HCID 23145656, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

15 mg of 2,5-difluoro-phenol and 28 mg of cesium carbonate were added to an N-methylpyrrolidinone (0.5 ml) solution of 26 mg of pyrazine-2-carboxylic acid (5-fluoro-4-(6-methanesulfonyl-pyridin-3-yloxy)-2-nitro-phenyl)-amide obtained in (step 1), and the reaction liquid was stirred at 90° C. for 15 minutes, and 100 mg of tin(II) chloride dihydrate was added to the reaction liquid. The reaction liquid was stirred at 90° C. for 1 hour, and ethyl acetate and aqueous saturated sodium bicarbonate were added to it. The deposit was removed through filtration, the solvent was evaporated away under reduced pressure, and the residue was 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 pale yellow solid.

Aufarbeitung

  1. customobtained in (step 1)
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. stirringwas stirred at 90° C. for 1 hour
  5. customThe deposit was removed through filtration
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe residue was purified 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

Quellen und Nachweise

ORD-Eintrag
ord-8ebde3e6dcdb4147af6b0162605e6e43
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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