Cesium carbonate → HCID 178477281, Verbindung
Reaktionsgleichung
Cl[C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5].[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([OH:33])[CH:30]=[CH:31][CH:32]=1)[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:24]([S:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[O:33][C:2]1[N:22]=[CH:21][C:20]([F:23])=[CH:19][C:3]=1[C:4]([NH:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14](=[O:18])[CH2:15][O:16][CH3:17])[CH2:9][CH2:8]1)=[O:5])[CH3:25]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 55 °C
Versuchsvorschrift
2-Chloro-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (110 mg, 0.32 mmol), 3-ethylsulfanyl-phenol (54 mg, 0.35 mmol) and caesium carbonate (156 mg, 0.48 mmol) were suspended in dimethylformamide (2 ml) and the reaction was heated to 55° C. and stirred at this temperature under nitrogen for 18 h. The reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml) and the organic phase was collected by passing the mixture through a chemelute cartridge, washing with ethyl acetate (20 ml). The solvent was removed under reduced pressure and the residue was triturated with diethylether (5 ml) to give 2-(3-ethylsulfanyl-phenoxy)-5-fluoro-N-[cis-4-(2-methoxy-acetylamino)-cyclohexyl]-nicotinamide (57 mg) as an off-white solid.
Aufarbeitung
- customThe reaction was quenched with sat. ammonium chloride solution (1 ml) and water (1 ml)
- customthe organic phase was collected
- washwashing with ethyl acetate (20 ml)
- customThe solvent was removed under reduced pressure
- customthe residue was triturated with diethylether (5 ml)
Quellen und Nachweise
- ORD-Eintrag
- ord-d7b665c7e3dd44eb932dd1632f0011af
- Quelldatensatz
- uspto-grants-2006_11
- Patentnummer
- US07141586B2
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