Butyryl chloride → N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-butyramide

HRID 2180003Notes

Reaction equation

HRID 2180003 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:7][O:8][C:9]1[C:14]([NH2:15])=[CH:13][C:12]([CH3:16])=[C:11]([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:10]=1.C(N(C(C)C)CC)(C)C.CCOC(C)=O>C(Cl)Cl>[CH3:7][O:8][C:9]1[C:14]([NH:15][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[CH:13][C:12]([CH3:16])=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:26])([F:27])[F:25])=[CH:19][C:18]=2[O:28][CH3:29])[N:10]=1

Participants

6

Reactant 4

HCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 224900462-Methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine

Product 1

HCID 22490068N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Butyryl chloride (0.174 ml, 1.675 mmol) is added to a solution of 2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-ylamine (0.5 g, 1.523 mmol) and diisopropylethylamine (0.32 ml, 1.83 mmol) in CH2Cl2 (10 ml) at room temperature. The mixture is stirred at room temperature for 30 minutes. EtOAc (50 ml) is added and the mixture is washed with 1 N NaOH and brine. After drying over Na2SO4, the solvent is removed under reduced pressure. The residue is purified by flash column chromatography (hexane/EtOAc=4:1) to give N-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-butyramide. Rf (hexane/EtOAc=4:1)=0.46.

Workup

  1. washthe mixture is washed with 1 N 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-877cadd0ccdc405a968840911b6e2b28
Source dataset
uspto-grants-2005_05
Patent number
US06887875B2

Reaction notes

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