Cesium carbonate → HCID 178503226, Verbindung

HRID 724273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 724273
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([C:17]2[C:18](Cl)=[N:19][CH:20]=[C:21]([F:23])[CH:22]=2)=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:26][S:27][C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([C:17]2[C:18]([O:34][C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([S:27][CH3:26])[CH:29]=3)=[N:19][CH:20]=[C:21]([F:23])[CH:22]=2)=[O:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 99204073-(Methylsulfanyl)phenolHCID 178454040HCID 178454040, Verbindung

Produkt 1

HCID 178503226HCID 178503226, VerbindungAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

{cis-4-[(2-Chloro-5-fluoro-pyridine-3-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester (5.44 g, 14.6 mmol), 3-methylsulfanylphenol (2.05 g, 14.6 mmol) and caesium carbonate (7.15 g, 21.9 mmol) were suspended in dimethylformamide (100 ml) and the reaction was heated to 65° C. and stirred at this temperature under nitrogen for 18 h, then at room temperature for 48 h. The reaction was cooled to room temperature, concentrated under reduced pressure and the residue was diluted with water (75 ml). It was then extracted with ethyl acetate (3×100 ml) and the combined organic extracts were washed with water (2×30 ml), brine (30 ml), dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with pentane:ether (50:50 changing to 45:55 then 40:60, by volume) to give (cis-4-{[-5-fluoro-2-(3-methylsulfanyl-phenoxy)-pyridine-3-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester (3.69 g) as a white solid.

Aufarbeitung

  1. waitat room temperature for 48 h
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionthe residue was diluted with water (75 ml)
  5. extractionIt was then extracted with ethyl acetate (3×100 ml)
  6. washthe combined organic extracts were washed with water (2×30 ml), brine (30 ml)
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel eluting with pentane:ether (50:50 changing to 45:55

Quellen und Nachweise

ORD-Eintrag
ord-98e8a03dbbe347c7a1582481e20ef37f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141586B2

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