1-(3-(Pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine → HCID 178511875, compound

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Reaction Steps

To a stirred solution of 1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-amine (115 mg, 0.443 mmol) in ethanol (6 ml) under argon was added methyl thiophene-2-carbimidothioate hydroiodide (253 mg, 0.887 mmol). The reaction mixture was stirred overnight at room temperature. The mixture was then diluted with water and sodium carbonate and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel using ethyl acetate, followed by 5-10% (2M NH3 in methanol) in dichloromethane as eluent to give the desired N-(1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide (119 mg, 0.323 mmol, 72.8% yield). 1H NMR (DMSO-d6) δ 7.67 (d, J=3.6 Hz, 1H), 7.55 (d, J=5 Hz, 1H), 7.06 (dd, J=5, 3.6 Hz, 1H), 6.58 (brs, 2H), 6.48 (s, 1H), 6.27 (brs, 2H), 3.26-3.17 (m, 4H), 2.66 (t, J=6.3 Hz, 2H), 2.45-2.40 (m, 6H), 1.89-1.81 (m, 2H), 1.70-1.62 (m, 6H). ESI-MS (m/z, %) 369 (MH+, 47), 185 (100). ESI-HRMS calculated for C21H29N4S (MH+), calculated: 369.2122, observed: 369.2107. HPLC purity: >95%.

Provenance & Evidence