HCID 56593710, compound → HCID 178511902, compound

Participants

Reaction Steps

Compound 109 (0.4 g, 1.485 mmol) in dry ethanol (10 mL) was treated with Pd—C (˜0.05 g), purged with hydrogen gas and stirred for 36 h at room temperature under hydrogen atm (balloon pressure). The reaction was filtered through celite bed and washed with ethanol (2×5 mL). The combined ethanol layer was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.84 g, 2.970 mmol) at room temperature and stirred for over night (14 h). The solvent was evaporated, crude was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 112 (0.4 g, 77%) as a solid. mp 144-146° C.; 1H NMR (DMSO-d6) δ 1.20-1.28 (m, 1H), 1.56-1.74 (m, 3H), 2.62-2.72 (m, 1H), 2.79-2.92 (m, 3H), 3.09-3.34 (m, 4H), 6.30 (s, 2H), 6.53 (d, 1H, J=8.4 Hz), 6.79 (s, 1H), 7.07-7.10 (m, 2H), 7.38 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=4.5 Hz), 7.72 (d, 1H, J=3.0 Hz), 10.61 (s, 1H); ESI-MS (m/z, %): 351 (MH+, 38), 176 (100); ESI-HRMS calculated for C20H23N4S (MH+), calculated: 351.1637; observed: 351.1637.

Provenance & Evidence