反应详情

To a stirred solution of 2-((3-(6-amino-3,4-dihydroquinolin-1(2H)-yl)propyl)(methyl)amino)ethanol (67 mg, 0.254 mmol) in ethanol (4 ml) under argon was added methyl thiophene-2-carbimidothioate hydroiodide (145 mg, 0.509 mmol). The resulting suspension was stirred overnight at room temperature. The reaction mixture was then diluted with water and aqeuous sodium carbonate (sat.) then extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel eluting with ethyl acetate, followed by 5-10% (2M NH3 in methanol) in a 1:1 mixture of ethyl acetate and dichloromethane. 1H NMR (DMSO-d6) δ 7.67 (d, J=3.3 Hz, 1H), 7.55 (d, J=5.1 Hz, 7.07 (t, J=4.4 Hz, 1H), 6.55 (m, 2H), 6.48 (s, 1H), 6.23 (brs, 2H), 4.35 (t, J=5.4 Hz, 1H), 3.51-3.44 (m, 2H), 3.24-3.17 (m, 4H), 2.66 (t, J=6.45, 2H), 2.41-2.33 (m, 4H), 2.17 (s, 3H), 1.89-1.81 (m, 2H), 1.63 (quint, J=7 Hz, 2H). ESI-MS (m/z, %) 373 (MH+, 100), 258 (31), 187 (49), 127 (42). ESI-HRMS calculated for C20H29N40S (MH+), calculated: 373.2056, observed: 373.2052.

1. extractionthen extracted with dichloromethane (3×)
2. customThe combined organics were dried
3. filtrationfiltered
4. concentrationconcentrated
5. customchromatographed on silica gel eluting with ethyl acetate
6. additionfollowed by 5-10% (2M NH3 in methanol) in a 1:1 mixture of ethyl acetate and dichloromethane