Pyridine → 1-{4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazin-1-yl}ethanone

HRID 2105988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2105988
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([CH2:9][C:10]([OH:28])([CH2:15][C:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])([CH3:18])[CH3:17])[C:11]([F:14])([F:13])[F:12])[CH2:3]1.N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[F:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH3:27])=[C:19]([C:16]([CH3:18])([CH3:17])[CH2:15][C:10]([OH:28])([C:11]([F:12])([F:13])[F:14])[CH2:9][N:4]2[CH2:3][CH:2]([CH3:1])[N:7]([C:35](=[O:37])[CH3:36])[CH:6]([CH3:8])[CH2:5]2)[CH:24]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57809802HCID 57809802, Verbindung

Produkt 1

HCID 103664031-{4-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylpiperazin-1-yl}ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(3,5-dimethylpiperazin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (18 mg) in methylene chloride (1 mL) was added pyridine (55.8 μL) followed by acetic anhydride (43.4 μL). The resulting mixture was stirred overnight, quenched with saturated aqueous sodium bicarbonate solution and extracted twice with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography with silica gel (eluted with 50% ethyl acetate-hexanes) to give the title compound as a clear oil (20 mg).

Aufarbeitung

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography with silica gel (eluted with 50% ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cdce3900379f41e99cd1e873895f3daa
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

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