Methanol → {4-[6-(2-Phenylethanesulfinyl)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanone

HRID 2108370Notizen

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I([O-])(=O)(=O)=O.[Na+].C[OH:8].[CH2:9]([S:17][C:18]1[N:23]=[N:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]([F:41])([F:40])[F:39])=[O:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[C:11]1([CH2:10][CH2:9][S:17]([C:18]2[N:23]=[N:22][C:21]([N:24]3[CH2:25][CH2:26][N:27]([C:30]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([F:41])([F:40])[F:39])=[O:31])[CH2:28][CH2:29]3)=[CH:20][CH:19]=2)=[O:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 11155686[4-(6-Phenethylsulfanylpyridazin-3-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanoneHCID 23667635Sodium periodate

Produkt 1

HCID 11179294{4-[6-(2-Phenylethanesulfinyl)pyridazin-3-YL]piperazin-1-YL}-(2-trifluoromethylphenyl)methanoneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To an ice-cold solution of sodium periodate (0.025 g, 0.12 mmol) in 1:1 mixture of water and methanol was added [4-(6-phenethylsulfanylpyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone. The reaction mixture was stirred at room temperature over night, diluted with water and then extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous MgSO4 and then concentrated in vacuo. The residue was purified by column chromatography to yield the title compound as a white solid (41 mg, 69.2%). 1H NMR (400 MHz, CDCl3) δ 7.86, 7.75, 7.63-7.66, 7.56-7.59, 7.37, 7.25-7.28, 7.21-7.17, 7.07-7.09, 4.04-4.10, 3.83-3.91, 3.70-3.80, 3.45-3.35, 3.26-3.30, 3.2-3.15.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-501fbef82eed46088ea185458f802c95
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514436B2

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