HCID 178480390, compound → HCID 178482191, compound

Participants

Reaction Steps

A solution of compound 5 (250 mg, 0.533 mmol) in MeOH (10 mL) and 1M HCl (10 mL) was refluxed for half an hour and then concentrated. The residue was partitioned between 3N NaOH (50 mL) and CH2Cl2 (25 mL) and the product was extracted into CH2Cl2 (2×25 mL). The combined organic layers were dried (Na2SO4), and concentrated. This residue was subjected to flash chromatography on silica gel: 2% methanol: 98% CH2Cl2 followed by 2.5% 2M ammonia in methanol; 97.5% CH2Cl2 to give a yellow-brown solid. (108 mg, 55% yield) 1H NMR (DMSO-d6) δ 7.67 (d, J=3.0 Hz, 1H), 7.54 (d, J=5.1 Hz, 1H), 7.07 (dd, J=3.9, 5.1 Hz), 6.62-6.47 (m, 3H), 6.21 (s, 2H), 3.57-3.50 (m, 1H), 3.11 (t, J=5.4 Hz, 2H), 2.63 (t, J=6.3 Hz, 2H), 2.28 (s, 3H), 2.24-2.20 (m, 1H), 1.98-1.92 (m, 2H), 1.82-1.77 (m, 2H), 1.70-1.65 (m, 2H), 1.59-1.47 (m, 2H), 1.24-1.11 (m, 2H). ESI-MS (m/z, %): 369 (MH+, 82), 338 (100), 258 (21), 185 (50), 148 (64), 140 (46); ESI-HRMS calculated for C21H29N4S (MH+): 369.2107, Observed: 369.2104; HPLC purity: 95.3%.

Provenance & Evidence