HCID 178480163, compound → HCID 178511883, compound

Participants

Reaction Steps

A solution of compound 3 (0.40 g, 1.531 mmol) and Pd—C (0.162 g, 0.153 mmol, 10% wt) in dry ethanol (5 mL) was purged with hydrogen gas. The reaction was stirred at room temperature over night under hydrogen atm. (balloon pressure). Then the reaction mixture was filtered through a celite pad and washed with ethanol (35 mL). The filtrate (compound 4) was treated with imidate 5 (0.873 g, 3.06 mmol) and stirred over night at room temperature. The reaction was diluted with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×25 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was subjected to flash chromatography on silica gel: 2% methanol: 98% CH2Cl2 followed by 5% 2M NH3 in methanol: 95% CH2Cl2, to give a greenish/yellow solid (230 mg, 44%). 1H-NMR (DMSO-d6) δ 7.68 (dd, J=0.9, 3.6 Hz, 1H), 7.55 (dd, J=0.9, 5.1 Hz, 1H), 7.07 (dd, J=3.6, 4.8 Hz, 1H), 6.62 (s, 1H), 6.50-6.45 (m, 2H), 6.23 (s, 2H), 3.33-3.27 (m, 2H), 3.11 (t, J=6.9 Hz, 2H), 2.84 (t, J=8.1 Hz, 2H), 2.62 (t, J=7.5, 2H), 2.55-2.45 (m, 4H), 1.70-1.65 (m, 4H); ESI-MS (m/z, %): 341 (MH+, 100), 244 (45), 127 (57), 98 (38); ESI-HRMS calculated for C19H25N4S (MH+): Calculated: 341.1794, Observed: 341.1788; HPLC purity: 95.3%.

Provenance & Evidence