2-bromo-N-(3-methylphenyl)acetamide → HCID 86655291, compound

HRID 2192373Notes

Reaction equation

HRID 2192373 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:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=1)=[O:28]>C(#N)C>[Br-:25].[C:19]1([C:12]2([C:10]([O:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N+:1]([CH2:26][C:27](=[O:28])[NH:29][C:30]5[CH:31]=[C:32]([CH3:36])[CH:33]=[CH:34][CH:35]=5)([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 2255282-bromo-N-(3-methylphenyl)acetamideHCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655291HCID 86655291, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in acetonitrile (1 mL) was added 2-bromo-N-m-tolyl-acetamide (Example 47a) (38 mg). The reaction was stirred at room temperature for 26 hours and the acetonitrile was removed under reduced pressure. The material was purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to afford the title compound (37 mg) as a colourless foam.

Workup

  1. customthe acetonitrile was removed under reduced pressure
  2. customThe material was purified by silica gel chromatography
  3. washeluting with 0-10% MeOH/dichloromethane

Sources & evidence

ORD record
ord-8a8b919f2f084399907ad2c15e3c9d75
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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