Sodium Hydroxide → [4-(6-Phenethylsulfanylpyridazin-3-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanone

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Reaktionsgleichung

Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:26]1([CH2:32][CH2:33][SH:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[Na+]>O1CCOCC1.O>[CH2:33]([S:34][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)[CH2:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 105 °C

Versuchsvorschrift

A mixture of [4-(6-chloro pyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)-methanone (0.089 g, 0.240 mmol), 2-phenylethanethiol (0.049 g, 0.36 mmol) and sodium hydroxide (9.6 mg) in 5 mL 1,4-dioxane was heated at 100-110° C. overnight. The reaction mixture was cooled to room temperature, diluted with 20 mL of water, and then extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulphate, then concentrated in vacuo. The residue was pirified by column chromatography to yield the title compound as a white solid (50 mg, 43.7% yield). 1H NMR (400 MHz, CDCl3) δ 7.65, 7.52-7.55, 7.47-7.48, 7.27, 7.12-7.22, 7.03, 6.76, 3.89-3.94, 3.79-3.84, 3.54-3.61, 3.49-3.51, 3.45, 3.17-3.25, 2.97.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with dichloromethane
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-ec86235b38ef4c3aae0868ce591f5401
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07514436B2

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