Ammonia → HCID 178480392, compound

Participants

Reaction Steps

A solution of 1-(1-methylpyrrolidin-3-yl)-1,2,3,4-tetrahydroquinolin-6-amine (80 mg, 0.35 mmol) in 8 mL ethanol was treated with methyl thiophene-2-carbimidothioate hydroiodide (197 mg, 0.69 mmol) and stirred overnight at room temperature. The mixture was diluted with CH2Cl2 (10 mL) and argon was bubbled through the solution for 20 minutes. The solution was partitioned between CH2Cl2 (100 mL) and 1N NaOH (20 mL). After extraction, the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give a dark residue which was subjected to flash chromatography on silica gel using 2.5% MeOH/CH2Cl2 then 5% 2M NH3 in MeOH/CH2Cl2. A light brown solid was obtained. This compound was converted to the dihydrochloride salt (95 mg, 65.6%). 1H-NMR (DMSO-d6) δ 7.67 (d, J=3.3 Hz, 1H), 7.55 (d, J=5.1 Hz, 1H), 7.08-7.06 (m, 1H), 6.70 (d, J=8.7 Hz, 1H), 6.55-6.50 (m, 2H), 6.29 (brs, 2H), 4.46-4.37 (m, 1H), 3.21-3.15 (m, 2H), 2.74-2.69 (m, 4H), 2.50-2.43 (m, 2H), 2.25 (s, 3H), 2.15-2.04 (m, 1H), 1.86-1.67 (m, 3H). MS (ESI): 341.2 (M+1). ESI-HRMS calculated for C19H25N4S (MH+): 341.1794, Observed: 341.1788.

Provenance & Evidence