Acetanilide, 2-bromo-N-methyl- → HCID 86655286, compound

HRID 2192365Notes

Reaction equation

HRID 2192365 reaction equation
Br[CH2:2][C:3]([N:5]([CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22]([C:24]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:14]2>CC#N>[CH:22]([O-:23])=[O:21].[CH3:12][N:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([CH2:2][N+:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22]([C:24]1([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:14]2)=[O:4]

Participants

4

Reactant 2

HCID 34495Acetanilide, 2-bromo-N-methyl-HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

Product 1

HCID 86655286HCID 86655286, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-N-methyl-N-phenyl-acetamide ((Example 39a) (38 mg) and 1-phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (50 mg) in 1 mL MeCN was stirred at room temperature for 48 h. The volatiles were evaporated and the residue purified by silica gel chromatography eluting with 0-10% MeOH/dichloromethane. Further purification by reverse phase HPLC eluting with 20-90% MeCN/H2O containing 0.1% formic acid gave the title compound (17 mg) as a colourless gum.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue purified by silica gel chromatography
  3. washeluting with 0-10% MeOH/dichloromethane
  4. customFurther purification by reverse phase HPLC
  5. washeluting with 20-90% MeCN/H2O containing 0.1% formic acid

Sources & evidence

ORD record
ord-1ce15e96212e43e19b1de0e4852eb353
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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