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

HRID 2192377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192377
[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]([CH3:36])=[CH:34][CH:35]=1)=[O:28]>CC#N>[Br-:25].[CH3:36][C:33]1[N:32]=[N:31][C:30]([NH:29][C:27]([CH2:26][N+:1]23[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:28])=[CH:35][CH:34]=1

Komponenten

4

Edukt 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 673108012-Bromo-N-(6-methyl-pyridazin-3-yl)-acetamide

Produkt 1

HCID 86655295(R)-1-[(6-Methyl-pyridazin-3-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (0.20 mmol) and 2-bromo-N-(6-methyl-pyridazin-3-yl)-acetamide (Example 49a (0.20 mmol) were stirred together in anhydrous MeCN at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the yellow solid purified by flash silica gel column chromatography eluting with 0-15% MeOH/dichloromethane to give the title compound (65 mg) as a tan solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe yellow solid purified by flash silica gel column chromatography
  3. washeluting with 0-15% MeOH/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-94e901d8442f4c03a04b62c79ec92ffe
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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