Ammonia → HCID 178511880, compound

Participants

Reaction Steps

A solution of 6-amino-1-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydroquinolin-2(1H)-one (165 mg, 0.636 mmol) in 5 mL of ethanol was treated with methyl thiophene-2-carbimidothioate hydroiodide (363 mg, 1.27 mmol) and stirred for 18 hours at room temperature. The mixture was partitioned between CH2Cl2 (50 mL) and saturated sodium bicarbonate (10 mL). The aqueous layer was extracted with an additional 20 mL CH2Cl2. The combined organic layers were dried over sodium sulfate and concentrated to give a yellow residue which was subjected to flash chromatography on a Biotage system using 5-10% 2M NH3 in MeOH/CH2Cl2 to give a yellow solid. Yield: 157 mg of yellow oil (68%). 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), 4.86 (br s, 2H), 4.12-4.06 (m, 2H), 2.88-2.83 (m, 2H), 2.75-2.70 (m, 2H), 2.65-2.60 (m, 6H), 1.82-1.78 (m, 4H). MS (ESI): 369.2 (M+1). ESI-HRMS calculated for C20H25N4SO (MH+): 369.1743, Observed: 369.1731.

Provenance & Evidence