Propionyl chloride → N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxyphenyl)-5-methyl-pyridin-3-yl]-propionamide

HRID 1354244Notes

Reaction equation

HRID 1354244 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH3:6][O:7][C:8]1[C:13]([NH2:14])=[CH:12][C:11]([CH3:15])=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[O:27][CH3:28])[N:9]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[CH3:6][O:7][C:8]1[C:13]([NH:14][C:1](=[O:4])[CH2:2][CH3:3])=[CH:12][C:11]([CH3:15])=[C:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:25])([F:26])[F:24])=[CH:18][C:17]=2[O:27][CH3:28])[N:9]=1

Participants

6

Reactant 3

HCID 62324Propionyl chlorideHCID 81531DiisopropylethylamineHCID 224900462-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine

Product 1

HCID 21104864N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxyphenyl)-5-methyl-pyridin-3-yl]-propionamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propionyl chloride (0.058 ml, 0.67 mmol) is added to a solution of 2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine (0.2 g, 0.61 mmol) and diisopropylethylamine (0.13 ml, 0.73 mmol) in CH2Cl2 (1.5 ml) at room temperature. The mixture is kept at room temperature for 3 hours, and is then diluted with EtOAc The mixture is washed with 1N NaOH and brine. After drying over Na2SO4, the solvent is removed under reduced pressure and the residue is purified by flash column chromatography (hexane/EtOAc=4:1) to give the N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-propionamide. Rf (hexane/EtOAc=4:1)=0.2.

Workup

  1. washis washed with 1N NaOH and brine
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent is removed under reduced pressure
  4. customthe residue is purified by flash column chromatography (hexane/EtOAc=4:1)

Sources & evidence

ORD record
ord-c2d0c0660251411b9a67400e5a632fb4
Source dataset
uspto-grants-2007_05
Patent number
US07223778B2

Reaction notes

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