Water → N-[6-(Acetylamino)pyridin-3-yl]-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamide

HRID 2263173

Reaktionsgleichung

Reaktionsgleichung von HRID 2263173
[C:1]([NH:4][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].[CH3:20][C:21]1[S:25][C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:23][C:22]=1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([N:29]2[CH2:30][CH2:31][N:26]([C:24]3[S:25][C:21]([CH3:20])=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:23]=3)[CH2:27][CH2:28]2)=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 172338685-Methyl-4-phenyl-2-piperazinyl-1,3-thiazoleHCID 862452592,2,2-Trichloroethyl[6-(acetylamino)pyridin-3-yl]carbamate

Produkt 1

HCID 68779446N-[6-(Acetylamino)pyridin-3-yl]-4-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine-1-carboxamideAusbeute 47,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2,2,2-trichloroethyl [6-(acetylamino)pyridin-3-yl]carbamate (277 mg, 0.848 mmol), 1-(5-methyl-4-phenyl-1,3-thiazol-2-yl)piperazine (200 mg, 0.771 mmol) and diisopropylethylamine (0.148 ml, 0.848 mmol) in dimethylsulfoxide (2.6 ml) was stirred at 70° C. for 18 hours. Water was poured into the reaction solution, and the mixture 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 161 mg (47.8%) of the desired product 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 purified by silica gel column chromatography (ethyl acetate)
  6. customrecrystallized from a mixed solvent of hexane and tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-37c81f786d24455b9f77d935f0c91186
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07851473B2

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