Water → N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-N-propyl-propionamide

HRID 1354245Notes

Reaction equation

HRID 1354245 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[CH:9][C:8]([CH3:16])=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[O:28][CH3:29])[N:6]=1.I[CH2:31][CH2:32][CH3:33].O>CN(C=O)C>[CH3:3][O:4][C:5]1[C:10]([N:11]([CH2:31][CH2:32][CH3:33])[C:12](=[O:15])[CH2:13][CH3:14])=[CH:9][C:8]([CH3:16])=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[O:28][CH3:29])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21104864N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxyphenyl)-5-methyl-pyridin-3-yl]-propionamide

Product 1

HCID 21104863N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-N-propyl-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% NaH (23 mg, 0.58 mmol) is added to a solution of N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-propionamide (0.15 g, 0.39 mmol) in DMF (1 ml) at room temperature. After stirring at room temperature for 20 minutes, iodo propane (0.058 ml, 0.58 mmol) is added. The mixture is stirred at room temperature for 3 days. 20 ml of water is added and the mixture is extracted with EtOAc. The combined extracts are washed with brine and dried over Na2SO4. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography to give N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-N-propyl-propionamide. Rf (hexane/EtOAc=2:1)=0.42.

Workup

  1. stirringThe mixture is stirred at room temperature for 3 days
  2. extractionthe mixture is extracted with EtOAc
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-f8280af0d3a14ae1b2279362db9ff73a
Source dataset
uspto-grants-2007_05
Patent number
US07223778B2

Reaction notes

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