Methyl vinyl sulfone → HCID 59415936, Verbindung

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Reaktionsgleichung

[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2].[CH:44]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH2:45]>C(O)(C)C>[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24]([CH2:45][CH2:44][S:46]([CH3:49])(=[O:48])=[O:47])[CH2:23]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydroquinoline-3-carboxylate (Example 262, 0.150 g, 0.24 mmol) was taken up in isopropanol (2 mL) and methyl vinyl sulfone (0.026 mL, 0.29 mmol) was added. The reaction mixture was stirred at 100° C. for 18 h in a sealed vessel, then cooled to room temperature and the solvent was removed in vacuo and loaded directly onto silica. Purified by flash column chromatography on silica gel using (dichloromethane-methanol) gave (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-(2-(methylsulfonyl)ethyl)piperidin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (0.110 g, 62.5%).

Aufarbeitung

temperaturecooled to room temperature
customthe solvent was removed in vacuo
customPurified by flash column chromatography on silica gel using (dichloromethane-methanol)

Quellen und Nachweise

ORD-Eintrag: ord-b2f0a653cfb945a5be81474f3a08aa80
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08283361B2

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