1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 86655287, compound

HRID 2192367Notes

Reaction equation

HRID 2192367 reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[C:10]([F:12])[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][C:10]([F:12])=[CH:11][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 606519112-Bromo-N-(2,5-difluorophenyl)acetamide

Product 1

HCID 86655287HCID 86655287, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-N-(2,5-difluoro-phenyl)-acetamide (Example 41a) (47 mg) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (56 mg) in MeCN (1 mL) was stirred at room temperature for 30 h. The resulting precipitate was filtered off, washed with ether and dried at 50° C. under vacuum overnight to afford the title compound (65 mg) as a colourless solid.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with ether
  3. customdried at 50° C. under vacuum overnight

Sources & evidence

ORD record
ord-6c7caaf057dc4bbc9616f9eb30a6fab4
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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