2-bromo-N-(2-fluorophenyl)acetamide → (R)-1-[(2-Fluoro-phenylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192347Notes

Reaction equation

HRID 2192347 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[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[F:36])=[O:28]>C(#N)C>[Br-:25].[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[NH:29][C:27]([CH2:26][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:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2)=[O:28]

Participants

4

Reactant 2

HCID 34147132-bromo-N-(2-fluorophenyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 53311104(R)-1-[(2-Fluoro-phenylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (Example 14e) (56 mg) and 2-bromo-N-(2-fluoro-phenyl)-acetamide (Example 23a (44 mg) in acetonitrile (1 mL) was stirred at room temperature for 30 h. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum at 50° C. to give the title compound (52 mg) as a colourless solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ether
  3. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-23bb63ccca4345d3ba12ebd26fafab3c
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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