Water → N-pyridin-4-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2263018
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:15])OCC(Cl)(Cl)Cl)=[CH:3][CH:2]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[N:26]=[C:25]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[S:24][N:23]=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:30]2[CH2:29][CH2:28][N:27]([C:25]3[S:24][N:23]=[C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=4)[N:26]=3)[CH2:32][CH2:31]2)=[O:15])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 142572942,2,2-Trichloroethyl pyridin-4-ylcarbamateHCID 687780931-(3-Pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine

Produkt 1

HCID 68778017N-pyridin-4-yl-4-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixed solution of 2,2,2-trichloroethyl pyridin-4-ylcarbamate (198 mg, 0.735 mmol), 1-(3-pyridin-2-yl-1,2,4-thiadiazol-5-yl)piperazine (200 mg, 0.809 mmol) and diisopropylethylamine (0.139 ml, 0.809 mmol) in dimethyl sulfoxide (2.5 ml) was stirred at 80° C. for 3 hours. Water was poured to the reaction mixture, and the resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1). 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:methanol=9:1) and recrystallized from a mixed solvent of hexane and tetrahydrofuran to give 62.1 mg (23.0%) of the desired product as a solid.

Aufarbeitung

  1. extractionthe resulting solution was extracted with a mixed solution of ethyl acetate/tetrahydrofuran (1:1)
  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:methanol=9:1)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-2c37bade6558433a88e7f25d21d40baf
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

Notizen zur Reaktion

Wird geladen…