HCID 53392183, compound → HCID 178480166, compound

Participants

Reaction Steps

A solution of 6-amino-1-(2-(1-methylpyrrolidin-2-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (1.15 g, 4.21 mmol) in absolute ethanol (25 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (2.40 g, 8.42 mmol) and stirred at room temperature for 18 hours. The reaction was diluted with diethyl ether (150 mL) and the precipitate collected by vacuum filtration. The precipitate was washed with ether (50 mL). The yellow solid was dissolved in water (50 mL) and transferred to a separatory funnel. The reaction was treated with 1N NaOH (10 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give a yellow oil which was subjected to flash chromatography on silica gel using 0-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow foam. Yield: 1.11 g of yellow foam (69%). 1H-NMR (DMSO-d6) δ: 7.73 (d, J=3.0 Hz, 1H), 7.60 (d, J=5.4 Hz, 1H), 7.10-7.02 (m, 2H), 6.72-6.75 (m, 2H), 6.45 (br s, 2H), 3.91-3.80 (m, 2H), 2.96-2.90 (m, 1H), 2.82-2.78 (m, 2H), 2.19 (s, 3H), 2.08-1.80 (m, 6H), 1.66-1.49 (m, 4H).

Provenance & Evidence