HCID 59807111, compound → HCID 178463987, compound

Participants

Reaction Steps

A solution of 6-Amino-1-(3-diethylamino-propyl)-3,4-dihydro-1H-quinolin-2-one (0.058 g, 0.211 mmol) in dry ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.120 g, 0.421 mmol) at room temperature and the resulting mixture was stirred for 64 hours. The reaction was transferred to a separatory funnel and diluted with ethyl acetate (30 mL) and saturated sodium hydrogen carbonate (20 mL). The aqueous was partitioned twice more with ethyl acetate (2×20 mL). The combined organics were washed with brine and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 0-1: 10-9). The product 7 was dried under high vacuum. Yield: 35 mg of yellow solid (44%). 1H NMR (CDCl3) δ: 7.44 (d, J=5.4 Hz, 1H), 7.41 (d, J=3.3 Hz, 1H), 7.09 (t, J=4.2 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 6.88 (d, J=2.1 Hz, 1H), 6.84 (d, J=4.2 Hz, 1H), 4.90 (br s, 2H), 4.03-3.99 (m, 2H), 2.90-2.85 (m, 2H), 2.77-2.62 (m, 8H), 2.03-1.93 (m, 2H), 1.15 (t, J=7.2 Hz, 6H). MS (ESI): 385.2 (M+1). ESI-HRMS calculated for C21H29N4SO2 (MH+): 385.2056, Observed: 385.2040.

Provenance & Evidence