4-Fluoro-2-(trifluoromethyl)benzoyl chloride → 2-Trifluoromethyl-4-fluoro-n-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide mono-hydrochloride salt

HRID 30209

Reaktionsgleichung

Reaktionsgleichung von HRID 30209
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1.[F:17][C:18]([F:30])([F:29])[C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21]([Cl:23])=[O:22]>O1CCOCC1>[ClH:23].[F:29][C:18]([F:17])([F:30])[C:19]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:20]=1[C:21]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1)=[O:22]

Komponenten

4

Edukt 2

HCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 11401723(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

Produkt 1

HCID 179803422-Trifluoromethyl-4-fluoro-n-[6-(1-methyl-piperidin-4-ylcarbonyl)-pyridin-2-yl]-benzamide mono-hydrochloride saltAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Combine 2-amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.19 g, 0.87 mmol), 2-trifluoromethyl-4-fluoro-benzoyl chloride (0.395 g, 1.74 mmol), and 1,4-Dioxane (50 mL). Stir and heat the mixture at reflux. After 3 hr., cool the reaction mixture to ambient temperature and concentrate. Load the mixture onto an SCX column (10 g), wash with methanol, and elute with 2M ammonia/methanol. Concentrate the eluent to obtain the free base of the title compound as an oil (0.241 g, 68%). Dissolve the oil in methanol (5 mL) and treat with ammonium chloride (0.031 g, 0.59 mmol). Concentrate and dry under vacuum to obtain the title compound. HRMS Obs. m/z 410.1490, Calc. 410.1491; m.p. 145-150° C.

Aufarbeitung

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. concentrationconcentrate
  4. washLoad the mixture onto an SCX column (10 g), wash with methanol
  5. washelute with 2M ammonia/methanol
  6. concentrationConcentrate the eluent

Quellen und Nachweise

ORD-Eintrag
ord-f847ac18ec7740cbb61b28833705b48c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423050B2

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