Water → 4-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]-N-pyridin-3-ylpiperazine-1-carboxamide
Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[C:24]1[N:25]=[C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[S:27][CH:28]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[C:24]1[N:25]=[C:26]([N:29]2[CH2:34][CH2:33][N:32]([C:8]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[O:15])[CH2:31][CH2:30]2)[S:27][CH:28]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
A mixture of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (94.3 mg, 0.350 mmol), 1-[4-(2,3-dichlorophenyl)-1,3-thiazol-2-yl]piperazine (100 mg, 0.318 mmol) and diisopropylethylamine (0.111 ml, 0.636 mmol) in dimethyl sulfoxide (1.0 ml) was stirred at 70° C. for 3 days. Water was poured to the reaction mixture, 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 34.3 mg (24.8%) of the desired product as a solid. mp 132-133° C.
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-3b157c9d82c3428893d06d2e3f312508
- Quelldatensatz
- uspto-grants-2010_12
- Patentnummer
- US07851473B2
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