1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 86655284, compound

HRID 2192363Notes

Reaction equation

HRID 2192363 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[F:13])=[O:4].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([O:22][C:23]([C:25]1([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:15]2>CC#N>[Br-:1].[F:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([F:12])[C:6]=1[NH:5][C:3]([CH2:2][N+:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C@@H:16]([O:22][C:23]([C:25]1([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:15]2)=[O:4]

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 606517911196093-39-62×

Product 1

HCID 86655284HCID 86655284, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-N-(2,6-difluoro-phenyl)-acetamide (Example 38a) (42 mg) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in MeCN (1 mL) was stirred at room temperature for 19 h. A further 20 mg 2-bromo-N-(2,6-difluoro-phenyl)-acetamide was added and stirring continued for another 22 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 (41 mg) as a colourless foam.

Workup

  1. stirringstirring
  2. waitcontinued for another 22 h
  3. customThe volatiles were evaporated
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with 0-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-0316fee1ae28468ba4556d3c623f7a7b
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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