Sodium Bicarbonate → HCID 178462533, compound

Participants

Reaction Steps

A solution of 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-amine (0.32 g, 1.326 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.756 g, 2.65 mmol) at room temperature and stirred overnight (18 h). The reaction was basified with sat. NaHCO3 solution (30 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain N-(3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.37 g, 80%) as a solid. 1H NMR (DMSO-d6) δ 10.94 (s, 1H), 7.71 (d, 1H, J=3.3 Hz), 7.59 (s, 1H, J=5.1 Hz), 7.31 (dd, 1H, J=2.7, 5.4 Hz), 7.22 (s, 1H), 7.10 (t, 1H, J=4.8 Hz), 6.67 (d, 1H, J=8.4 Hz), 6.26 (brs, 2H), 6.05 (s, 1H), 3.10 (brs, 2H), 2.63 (t, 2H, J=5.1 Hz), 2.54-2.40 (m, 4H, merged with DMSO-peak), 1.06 (t, 3H, J=7.2 Hz); ESI-MS (m/z, %): 351 (MH+, 37), 294 (100); ESI-HRMS calculated for C20H23N4S (MH+), calculated: 351.1637; observed: 351.1636.

Provenance & Evidence