N-(2-Bromoethyl)pyridine-2-carboxamide → (R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-{2-[(pyridine-2-carbonyl)-amino]-ethyl}-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192399

Reaktionsgleichung

Reaktionsgleichung von HRID 2192399
[Br:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=[O:6].[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22]([C:24]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:14]2>C(#N)C>[Br-:1].[C:31]1([C:24]2([C:22]([O:21][C@@H:15]3[CH:16]4[CH2:19][CH2:20][N+:13]([CH2:2][CH2:3][NH:4][C:5]([C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=5)=[O:6])([CH2:18][CH2:17]4)[CH2:14]3)=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

4

Edukt 2

HCID 12983473N-(2-Bromoethyl)pyridine-2-carboxamide2×HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Produkt 1

HCID 67310911(R)-3-(1-Phenyl-cycloheptanecarbonyloxy)-1-{2-[(pyridine-2-carbonyl)-amino]-ethyl}-1-azonia-bicyclo[2.2.2]octane bromideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Pyridine-2-carboxylic acid (2-bromo-ethyl)-amide (Example 60a) (75 mg) was added to a solution of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (98 mg) in acetonitrile (2 mL). The reaction mixture was allowed to stir at room temperature for 16 h. A further 10 mg of pyridine-2-carboxylic acid (2-bromo-ethyl) -amide was added and the reaction mixture was stirred for 8 h. The volatiles were evaporated and the residue was purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give the title compound (55 mg) as a white solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 8 h
  2. customThe volatiles were evaporated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 0-10% MeOH/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-05219d2616354d0884b927f8c3737204
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329729B2

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