Water → 4-[4-(3-fluorophenyl)-1,3-thiazol-2-yl]-N-pyridazin-3-ylpiperidine-1-carboxamide

HRID 2263219

Reaktionsgleichung

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[N:2]=1.[F:16][C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[F:16][C:17]1[CH:18]=[C:19]([C:23]2[N:24]=[C:25]([CH:28]3[CH2:33][CH2:32][N:31]([C:8]([NH:7][C:3]4[N:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:29]3)[S:26][CH:27]=2)[CH:20]=[CH:21][CH:22]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A mixture of 2,2,2-trichloroethyl pyridazin-3-ylcarbamate (250 mg, 0.922 mmol), 4-[4-(3-fluorophenyl)-1,3-thiazol-2-yl]piperidine (220 mg, 0.839 mmol) and diisopropylethylamine (0.292 ml, 1.68 mmol) in dimethylsulfoxide (2.8 ml) was stirred at 70° C. for 6 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and ethyl acetate to give the desired product (141 mg, 43.7%) as a solid.

Aufarbeitung

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)
customrecrystallized from a mixed solvent of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-9a677cc7118f4e66b3e78751cd43ef57
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07851473B2

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