Piperidine → 5-[3-(3-Pyridyl)propylidene]-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357103

Reaktionsgleichung

Reaktionsgleichung von HRID 357103
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1CCCO.N1CC[CH2:35][CH2:34][CH2:33]1>C(O)C>[N:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH2:33][CH2:34][CH:35]=[C:18]2[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:19]2=[O:20])[CH:27]=1

Komponenten

5

Versuchsvorschrift

To a solution of 1.61 g (5.0 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione and 676 mg (5.0 mmol) of 3-(2-pyridyl)-1-propanol in 20 ml of ethanol, 43 mg (0.5 mmol) of piperidine-was added, followed by refluxing for 4 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=50/1) to yield 1.56 g (71.1%, yellow oily substance) of the desired product.

Aufarbeitung

  1. temperatureby refluxing for 4 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with purified water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, chloroform/methanol=50/1)

Quellen und Nachweise

ORD-Eintrag
ord-26978d1697f54bfe9c6e14b8ac1da42c
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840732

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