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

HRID 2180003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2180003
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-877cadd0ccdc405a968840911b6e2b28
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887875B2

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