1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → (R)-1-[(3-Fluoro-pyridin-4-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 2192387

Reaktionsgleichung

Reaktionsgleichung von HRID 2192387
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Cl:25][CH2:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][N:33]=[CH:32][C:31]=1[F:36])=[O:28]>CC#N>[Cl-:25].[F:36][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][C:30]=1[NH:29][C:27]([CH2:26][N+:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2)=[O:28]

Komponenten

4

Edukt 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 595037592-Chloro-N-(3-fluoro-pyridin-4-yl)-acetamide

Produkt 1

HCID 86655303(R)-1-[(3-Fluoro-pyridin-4-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (0.30 mmol) and 2-chloro-N-(3-fluoro-pyridin-4-yl)-acetamide (Example 54a) ( mmol) in MeCN (1.5 mL) were stirred together at room temperature overnight. The reaction mixture was concentrated in vacuo and the residue purified by silica gel chromatography eluting with 0-10% MeH/dichloromethane to give the title compound a white solid (110 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by silica gel chromatography
  3. washeluting with 0-10% MeH/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-81e00259864d446aa7ce5e7676d53b0d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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