Water → 3-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357001

Reaktionsgleichung

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[N:12]2[CH:13]=[CH:14][N:15]=[C:11]2[CH:10]=[CH:9][CH:8]=1.[S:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[N:15]1[CH:14]=[CH:13][N:12]2[C:7]([S:6][CH2:5][CH2:4][CH2:3][CH2:2][N:18]3[C:19](=[O:21])[CH2:20][S:16][C:17]3=[O:22])=[CH:8][CH:9]=[CH:10][C:11]=12

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 8.35 g (35.4 mmol) of 5-(4-chlorobutylthio)imidazo[1,2-a]pyridine and 4.15 g (35.4 mmol) of thiazolidine-2,4-dione in 200 ml of N,N-dimethylformamide, 5.30 ml (35.4 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, followed by heating at 80° C. for 16 hours. After cooling, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate). The resulting crude crystal was purified by recrystallization (solvent: chloroform/diethyl ether) to yield 10.01 g (88.0%, light orange crystal) of the desired product.

Aufarbeitung

temperatureAfter cooling
extractionextracted with ethyl acetate
washwashed with water
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent: ethyl acetate)
customThe resulting crude crystal was purified by recrystallization (solvent: chloroform/diethyl ether)

Quellen und Nachweise

ORD-Eintrag: ord-52a73c16fc07454983d12e6504b1120c
Quelldatensatz: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05840732

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