Water → 4-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]-N-pyrazin-2-ylpiperazine-1-carboxamide

HRID 2263204

Reaktionsgleichung

Reaktionsgleichung von HRID 2263204
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:26][CH:27]=2)=[CH:19][CH:18]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([N:28]3[CH2:29][CH2:30][N:31]([C:8]([NH:7][C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[O:15])[CH2:32][CH2:33]3)[S:26][CH:27]=2)=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 80272011-[4-(4-Fluorophenyl)-2-thiazolyl]piperazineHCID 687774032,2,2-Trichloroethyl pyrazin-2-ylcarbamate

Produkt 1

HCID 687790984-[4-(4-Fluorophenyl)-1,3-thiazol-2-yl]-N-pyrazin-2-ylpiperazine-1-carboxamideAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture if 2,2,2-trichloroethyl pyrazin-2-ylcarbamate (226 mg, 0.835 mmol), 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.760 mmol) and diisopropylethylamine (0.265 ml, 1.52 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 3 days. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was wash washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified silica gel column chromatography (ethyl acetate) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the desired product (99.7 mg, 34.0%) as a solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was wash
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-996151c7ada64869bae11e6fd38fd5fa
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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