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 2192377Notes

Reaction equation

HRID 2192377 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-94e901d8442f4c03a04b62c79ec92ffe
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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