Reaktionsgleichung
CN(C=O)C.[OH:6][C:7]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:15][CH:14]=2)[C:9](=[O:28])[CH:8]=1.[H-].[Na+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38]OS(C)(=O)=O)=[CH:34][N:33]=1>C(OCC)(=O)C>[F:31][C:32]1[N:33]=[CH:34][C:35]([CH2:38][O:6][C:7]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]4)=[CH:17][CH:18]=3)[C:9](=[O:28])[CH:8]=2)=[CH:36][CH:37]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Into a DMF solution (0.8 mL) of 4-hydroxy-1-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1H-pyridin-2-one (20 mg, 0.065 mmol), NaH (60% oiliness, 3 mg, 0.078 mmol) was added and stinred at room temeture for 20 minutes, followed by addition of DMF solution (0.2 mL) of 2-fluoro-5-methanesulfonyloxymethylpyridine (20 mg, 0.097 mmol), stirring at the same temperature for 2.5 hours and further an overnight stirring at 80° C. Ethyl acetate was added to the reaction liquid, which was then washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:10) to provide the title compound (12.5 mg, 45%).
Aufarbeitung
- stirringstirring at 80° C
- washwas then washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationConcentrating the solvent under reduced pressure
- customthe resulting residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:10)
Quellen und Nachweise
- ORD-Eintrag
- ord-cbf3b2d9f2324b2095cde49cb14f378d
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07732456B2
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