HCID 11160262, compound → HCID 178422093, compound

Participants

Reaction Steps

A solution of compound 24 (0.275 g, 1.266 mmol) in dry ethanol (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.72 g, 2.532 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 25 (0.32 g, 78%) as a foam. 1H NMR (DMSO-d6) δ 2.22 (s, 6H), 2.39 (s, 3H), 2.46-2.51 (m, 2H, merged with DMSO peak), 4.14 (t, 2H, J=6.9 Hz), 6.09 (s, 1H), 6.20 (brs, 2H), 6.61 (dd, 1H, J=1.2, 8.4 Hz), 6.87 (s, 1H), 7.09 (t, 1H, J=4.2 Hz), 7.27 (d, 1H, J=8.7 Hz), 7.57 (d, 1H, J=5.1 Hz), 7.70 (d, 1H, J=3.3 Hz); ESI-MS (m/z, %) 327 (MH+, 100); ESI-HRMS calculated for C18H23N4S (MH+), calculated: 327.1637; observed: 327.1653; HPLC purity: 98% by area.

Provenance & Evidence