Water → N-Pyridin-4-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamide

HRID 2263028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263028
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)=[CH:3][CH:2]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[S:23][N:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[N:1]1[CH:2]=[CH:3][C:4]([NH:7][C:8]([N:29]2[CH2:28][CH2:27][N:26]([C:24]3[S:23][N:22]=[C:21]([C:17]4[S:16][CH:20]=[CH:19][CH:18]=4)[N:25]=3)[CH2:31][CH2:30]2)=[O:15])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamateHCID 687780151-[3-(Thiophen-2-yl)-1,2,4-thiadiazol-5-yl]piperazine

Produkt 1

HCID 68780013N-Pyridin-4-yl-4-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine-1-carboxamideAusbeute 18,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (235 mg, 0.872 mmol), 1-[3-(2-thienyl)-1,2,4-thiadiazol-5-yl]piperazine (200 mg, 0.793 mmol) and diisopropylethylamine (0.152 ml, 0.872 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80° C. for 3.5 hours. Water was poured to the reaction mixture, and the resulting solution 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, followed by methanol:ethyl acetate=1:9) and recrystallized from a mixed solvent of hexane and ethyl acetate to give 54.9 mg (18.6%) of the desired product as a solid.

Aufarbeitung

  1. extractionthe resulting solution was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate, followed by methanol:ethyl acetate=1:9)
  6. customrecrystallized from a mixed solvent of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-77cfdb764d514997864e63caf0846972
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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