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Water → 4-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-3-ylpiperazine-1-carboxamide

HRID 2262986
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2262986
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)[CH:2]=1.[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[S:23][N:22]=2)=[CH:17]1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[O:16]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[C:24]([N:26]3[CH2:27][CH2:28][N:29]([C:8]([NH:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:15])[CH2:30][CH2:31]3)[S:23][N:22]=2)=[CH:17]1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 685753802,2,2-Trichloroethyl pyridin-3-ylcarbamateHCID 687778431-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]piperazine

Produkt 1

HCID 687774224-[3-(3-Furyl)-1,2,4-thiadiazol-5-yl]-N-pyridin-3-ylpiperazine-1-carboxamideAusbeute 28,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixed solution of 2,2,2-trichloroethyl pyridin-3-ylcarbamate (311 mg, 1.15 mmol), 1-[3-(3-furyl)-1,2,4-thiadiazol-5-yl]piperazine (300 mg, 1.27 mmol) and diisopropylethylamine (0.221 ml, 1.27 mmol) in dimethyl sulfoxide (3.8 ml) was stirred at 80° C. for 1 hour and half. 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) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 117 mg (28.3%) 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)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-898154617e2343afafc2c9107717f9cd
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851473B2

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