Hydrochloric Acid → 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-one

HRID 15076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15076
Cl.C1COCC1.[Si]([O:14][C@H:15]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=4)=[CH:31][C:30]3=[O:44])=[CH:25][CH:24]=2)[CH2:16]1)(C(C)(C)C)(C)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][O:35][C:32]2[CH:33]=[CH:34][N:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][N:17]4[CH2:18][CH2:19][C@H:15]([OH:14])[CH2:16]4)=[CH:28][CH:27]=3)[C:30](=[O:44])[CH:31]=2)=[N:38][CH:39]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 684307211-(4-{2-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl]ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one

Produkt 1

HCID 589649034-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-oneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

5N aqueous hydrochloric acid (2.4 mL, 12 mmols) was added to THF (2.4 mL) solution of 1-(4-{2-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl]ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (264.7 mg, 0.48 mmol), and stirred at room temperature for 2 hours. The reaction liquid was neutralized with 1N aqueous sodium hydroxide, extend with chloroform, washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was recrystallized from mixed solvent of ethyl acetate and heptane, to provide the title compound (199.8 mg, 95%).

Aufarbeitung

  1. customThe reaction liquid
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was recrystallized
  6. additionfrom mixed solvent of ethyl acetate and heptane

Quellen und Nachweise

ORD-Eintrag
ord-98a6e45d20c14bf48c3dda323bd78c88
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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