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Dimethyl Sulfoxide → N-{6-[Acetyl(methyl)amino]pyridin-3-yl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide

HRID 2263082
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2263082
[C:1]([N:4]([CH3:20])[C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])OCC(Cl)(Cl)Cl)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:21]1([C:27]2[N:31]=[C:30]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[C:1]([N:4]([CH3:20])[C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([N:35]2[CH2:36][CH2:37][N:32]([C:30]3[S:29][N:28]=[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:31]=3)[CH2:33][CH2:34]2)=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 27777601-(3-Phenyl-(1,2,4)thiadiazol-5-yl)-piperazineHCID 866254922,2,2-Trichloroethyl {6-[acetyl(methyl)amino]pyridin-3-yl}carbamate

Produkt 1

HCID 68779931N-{6-[Acetyl(methyl)amino]pyridin-3-yl]-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamideAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2,2,2-trichloroethyl {6-[acetyl(methyl)amino]pyridin-3-yl}carbamate (200 mg, 0.587 mmol), 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (145 mg, 0.587 mmol), diisopropylethylamine (0.102 ml, 0.587 mmol) and dimethylsulfoxide (4 ml) was stirred at 70° C. for 12 hours, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (101 mg, 39.3%) as a solid.

Aufarbeitung

  1. extractionthe mixture 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 recrystallized from a mixed solvent of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-66ff1180cdcd4791bdd75b5c41a1bda0
Quelldatensatz
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07851473B2

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