Triethylamine → HCID 178495808, Verbindung

Beteiligte Stoffe

Reaktionsschritte

To a suspension of the product of Example 126A (0.20 g, 1.1 mmol) in 25 mL THF was added Et3N (0.3 mL, 2.2 mmol) followed by the freshly prepared quinoline-4-carbonyl chloride. This mixture was warmed to reflux and allowed to stir for 18 hours. The material was then concentrated under reduced pressure and 10 mL EtOAc, 5 mL H2O and 5 mL NH4OH were added. The layers were separated and the aqueous layer was extracted 2×5 mL EtOAc. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via flash column chromatography (SiO2, 5% CH3OH in EtOAc) to afford the title compound (0.12 g, 0.35 mmol, 33% yield). 1H NMR (300 MHz, CD3OD) δ ppm 2.32 (d, J=0.7 Hz, 3H), 2.35 (d, J=0.7 Hz, 3H), 3.31 (s, 3H), 3.78 (t, J=5.3 Hz, 2H), 4.48 (t, J=5.1 Hz, 2H), 7.65 (ddd, J=8.5, 7.0, 1.2 Hz, 1H), 7.80 (ddd, J=8.4, 6.9, 1.4 Hz, 1H), 8.00 (d, J=4.4 Hz, 1H), 8.06-8.11 (m, 1H), 8.84 (ddd, J=8.5, 1.4, 0.7 Hz, 1H), 8.93 (d, J=4.4 Hz, 1H); MS (DCI/NH3) m/z 342 (M+H)+; Anal. calculated for C18H19N3O2S: C, 63.32; H, 5.61; N, 12.31. Found: C, 63.23; H, 5.46; N, 12.10.

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