Ethyl Methanesulfonate → 4-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-ethyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

HRID 15081

Reaktionsgleichung

Reaktionsgleichung von HRID 15081
CS(OCC)(=O)=O.C(#N)C.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C@@H:33]4[CH2:37][CH2:36][N:35]([CH:38](C)[CH3:39])[CH2:34]4)=[CH:28][CH:27]=3)[C:22](=[O:41])[CH:21]=2)=[N:16][CH:17]=1>C(Cl)(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:26]3[CH:27]=[CH:28][C:29]([O:32][C@@H:33]4[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34]4)=[CH:30][CH:31]=3)[C:22](=[O:41])[CH:21]=2)=[N:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 6113Ethyl Methanesulfonate2×HCID 6342AcetonitrileHCID 116119264-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-isopropyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

Produkt 1

HCID 115319734-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-ethyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-oneAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl methanesulfonate (0.45 mL) was added to acetonitrile solution of 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one (1.65 g, Example 122), and stirred at 80° C. for 2 hours. Additional ethyl methanesulfonate (0.45 mL) was added and stirred at 80° C. for further 2 hours, followed by cooling to room temperature. Chloroform was added to the reaction liquid which then was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:100-1:10-1:4). The residue was crystallized from mixed solvent of ethyl acetate and heptane to provide the title compound (660 mg).

Aufarbeitung

  1. stirringstirred at 80° C. for further 2 hours
  2. temperatureby cooling to room temperature
  3. washthen was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationConcentrating the solvent under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:100-1:10-1:4)
  7. customThe residue was crystallized
  8. additionfrom mixed solvent of ethyl acetate and heptane

Quellen und Nachweise

ORD-Eintrag
ord-01d3e5beed11407cab04b5788599f5fc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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