HCID 57474469, compound → HCID 178480210, compound

Participants

Reaction Steps

A solution of compound 136 (0.07 g, 0.283 mmol) in dry ethanol (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.16 g, 0.566 mmol) at room temperature and stirred for overnight (16 h). Solvent was evaporated, crude was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2 20 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 methanol: CH2Cl2, 5:95) to obtain compound 137 (0.09 g, 90%) as a solid. mp 115-117° C.; 1H NMR (DMSO-d6) δ 1.79-2.09 (m, 4H), 2.26 (s, 3H), 2.74-2.90 (m, 2H), 3.13-3.17 (m, 1H), 4.68 (dddd, 1H, J=4.8, 9.6, 9.6, 48.5 Hz), 6.23 (brs, 2H), 6.65 (d, 1H, J=8.1 Hz), 6.99 (s, 1H), 7.09 (t, 1H, J=4.2 Hz), 7.17 (d, 1H, J=1.5 Hz), 7.28 (d, 1H, J=8.4 Hz), 7.59 (d, 1H, J=5.1 Hz), 7.70 (d, 1H, J=3.3 Hz), 10.72 (s, 1H); ESI-MS m/z (%): 357 (MH+, 100), 179 (52); ESI-HRMS calculated for C19H22FN4S (MH+), Calculated: 357.1547, Observed: 357.1543.

Provenance & Evidence