8-Fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178480161, compound

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Reaction Steps

To a stirred solution of 8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-amine (580 mg, 2.091 mmol) in ethanol (15 ml) was added methyl thiophene-2-carbimidothioate hydroiodide (1193 mg, 4.18 mmol) as a solid. The resulting suspension was stirred overnight at room temperature under argon. The reaction mixture was then quenched with water and sodium carbonate (sat) and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated. The residue was then chromatographed in ethyl acetate, followed by 0-10% (2M NH3 in methanol) in dichloromethane, giving the desired N-(8-fluoro-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (485 mg, 1.255 mmol, 60.0% yield). 1H NMR (DMSO-d6) δ 7.71 (d, J=3 Hz, 1H), 7.57 (d, J=4.5 Hz, 1H), 7.07 (dd, J=4.8, 3.9 Hz, 1H), 6.44 (brs, 2H), 6.39-6.34 (m, 2H), 3.07-3.02 (m, 4H), 2.95-2.89 (m, 1H), 2.69-2.65 (m, 2H), 2.21 (s, 3H), 2.03-1.99 (m, 2H), 1.94-1.87 (m, 2H), 1.76-1.74 (m, 2H), 1.63-1.59 (m, 2H), 1.46-1.40 (m, 2H).

Provenance & Evidence