6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one → HCID 178483723, compound

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Reaction Steps

6-Amino-1-(2-(dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one (312 mg, 1.24 mmol) was stirred to dissolve in ethanol (15 mL). To this solution was added methyl thiophene-2-carbimidothioate hydroiodide (708 mg, 2.48 mmol). The resulting suspension was stirred for 2 days at room temperature. When TLC analysis showed that the reaction was finished, the mixture was diluted with water and aqueous sodium carbonate, then extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated and the crude product chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in ethyl acetate, then a second time using 20-80% MeCN in an aqueous buffer of ammonium carbonate and ammonium hydroxide adjusted to pH 10.6. Yield: 27 mg). 1H NMR (DMSO-d6) δ 2.14 (s, 6H), 2.44 (t, 2H, J=6.7 Hz), 2.49 (m, 2H, masked by DMSO peak), 2.80 (t, 2H, J=6.6 Hz), 3.95 (t, 2H, J=6.5 Hz), 6.61 (m, 4H), 7.09 (m, 1H), 7.62 (m, 1H), 7.75 (m, 1H). ESI-MS: 361 (MH+, 100), 316 (40), 158.6 (57), 136 (37).

Provenance & Evidence