1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-[(6-trifluoromethyl-pyridazin-3-ylcarbamoyl)-methyl]-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192303
[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.[Br:25][CH2:26][C:27]([NH:29][C:30]1[N:31]=[N:32][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:34][CH:35]=1)=[O:28]>C(#N)C>[Br-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][C:27](=[O:28])[NH:29][C:30]5[N:31]=[N:32][C:33]([C:36]([F:37])([F:39])[F:38])=[CH:34][CH:35]=5)([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 670277332-Bromo-N-(6-trifluoromethyl-pyridazin-3-yl)-acetamide

Produkt 1

HCID 53312358(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-[(6-trifluoromethyl-pyridazin-3-ylcarbamoyl)-methyl]-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 1e) (61.1 mg) and 2-bromo-N-(6-trifluoromethyl-pyridazin-3-yl)-acetamide (Example 3a) (53.0 mg) were dissolved in acetonitrile (2 mL) and left overnight. The solvent was evaporated and the product was purified by column chromatography on silica eluting with 10% methanol in dichloromethane to afford the titled compound (107 mg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe product was purified by column chromatography on silica eluting with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-3db47c941e0d4921905528307f54cf6b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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