HCID 57421478, compound → HCID 178422092, compound

Participants

Reaction Steps

A solution of compound 27 (0.37 g, 1.520 mmol) in dry ethanol (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.86 g, 3.040 mmol) at room temperature and stirred for overnight (16 h). The reaction was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 28 (0.43 g, 81%) as a foam. 1H NMR (DMSO-d6) δ 1.64-1.76 (m, 4H), 2.39 (s, 3H), 2.46-2.58 (m, 4H), 2.66 (t, 2H, J=7.2 Hz), 4.16 (t, 2H, J=7.2 Hz), 6.09 (s, 1H), 6.20 (brs, 2H), 6.61 (dd, 1H, J=1.8, 8.5 Hz), 6.87 (d, 1H, J=1.2 Hz), 7.08 (dd, 1H, J=3.9, 4.9 Hz), 7.27 (d, 1H, J=8.7 Hz), 7.57 (d, 1H, J=5.4 Hz), 7.70 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %) 253 (MH+, 100), 177 (56); ESI-HRMS calculated for C20H25N4S (MH+), calculated: 353.1794; observed: 353.1804; HPLC purity: 97% by area.

Provenance & Evidence