m-Chloroperbenzoic acid → 2-(2-Acetylaminopyridin-4-ylmethylsulfinyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

HRID 1984723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984723
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]([NH:15][C:16]1[CH:21]=[C:20]([CH2:22][S:23][C:24]2[C:29]([C:30]([NH:32][C:33]3[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=3)=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=2)[CH:19]=[CH:18][N:17]=1)(=[O:14])[CH3:13]>C(Cl)Cl.C(OCC)(=O)C>[C:12]([NH:15][C:16]1[CH:21]=[C:20]([CH2:22][S:23]([C:24]2[C:29]([C:30]([NH:32][C:33]3[CH:34]=[C:35]([CH3:40])[CH:36]=[C:37]([CH3:39])[CH:38]=3)=[O:31])=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:9])[CH:19]=[CH:18][N:17]=1)(=[O:14])[CH3:13]

Komponenten

5

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 111889642-(2-Acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide

Produkt 1

HCID 231508782-(2-Acetylaminopyridin-4-ylmethylsulfinyl)-N-(3,5-dimethylphenyl)pyridine-3-carboxamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

m-Chloroperbenzoic acid(75%, 60 mg, 0.26 mmol) was added to a solution of 2-(2-acetylaminopyridin-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (Compound No. 4-1, 60 mg, 0.15 mmol) in methylene chloride (3 mL) under ice-cooling, and the mixture was stirred for 1 hour. The reaction mixture was diluted with ethyl acetate (30 mL), the whole was washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) twice and brine (10 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the precipitated solid was filtered off with ethyl acetate to give 30 mg of the target compound as a colorless solid. (Yield 48%)

Aufarbeitung

  1. washthe whole was washed with saturated aqueous sodium hydrogen carbonate solution (10 mL) twice
  2. dry with materialbrine (10 mL), and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8bdfe4c71b694f21b3f8c41700195319
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544703B2

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