Water → HCID 58981775, compound

HRID 1727933Notes

Reaction equation

HRID 1727933 reaction equation
[C:1]1([CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:8][CH2:9][O:10][C:11](=[O:36])[C:12]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[CH3:25])=[C:16]([C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:27])[C:15]([CH3:34])=[N:14][C:13]=2[CH3:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:43](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[C:1]1([CH:7]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:8][CH2:9][O:10][C:11](=[O:36])[C:12]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=3[CH3:25])=[C:16]([C:26]([N:28]3[CH2:33][CH2:32][N:31]([CH3:43])[CH2:30][CH2:29]3)=[O:27])[C:15]([CH3:34])=[N:14][C:13]=2[CH3:35])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58981779HCID 58981779, compound

Product 1

HCID 58981775HCID 58981775, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

169 mg (0.301 mmol) of 4-(2,4-dimethylphenyl)-2,6-dimethyl-5-(piperazine-1-carbonyl)nicotinic acid (3,3-diphenylpropyl) ester was dissolved in 10 ml of DMF. 62.4 mg (01.301 mmol) of potassium carbonate was added and stirred for 30 minutes. 51.3 mg (0.361 mmol) of methyl iodide was added under cooling with ice and stirred at the same temperature for 1 hour. The reaction mixture was further stirred for 10 minutes after adding water. After evaporating DMF under reduced pressure, the reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol =50/1 to 10/1) to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringstirred at the same temperature for 1 hour
  3. stirringThe reaction mixture was further stirred for 10 minutes
  4. customAfter evaporating DMF under reduced pressure
  5. additionthe reaction mixture was diluted with ethyl acetate
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol =50/1 to 10/1)

Sources & evidence

ORD record
ord-df21487e39f848b0871641330d13fe32
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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