1-[Bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole → 1-[Bis-(3-hydroxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole

Participants

Reaction Steps

10% Pd/C (80 mg) was added to a solution of 1-[bis-(3-benzyloxy-4-methoxyphenyl)methyl]-1H-[1,2,4]triazole (1.65 g, 3.25 mmol) in THF/MeOH (1:1, 200 mL). The solution was stirred under an atmosphere of H2 (provided by addition from a balloon) overnight. The excess H2 was removed and the reaction mixture was filtered through Celite® washing with THF and MeOH, then the solvent was removed in vacuo. The crude product was purified using Flashmaster II (EtOAc/Hexane) to give the title compound STX1003 (0.86 g, 81%, mp 217.5-219° C.) as a white solid; δH (270 MHz, d6-DMSO) 9.08 (2H, s, 2×OH), 8.47 (1H, s, NCHN), 8.03 (1H, s NCHN), 6.88 (2H, d, J=8.4, ArH), 6.76 (1H, s, CH), 6.64 (2H, s, ArH), 6.57 (2H, d, J=8.4, ArH), 3.74 (6H, s, 2×CH3); δC (68 MHz, d6-DMSO) 151.8 (CH), 147.3 (2×C), 146.3 (2×C), 144.0 (CH), 130.1 (2×C), 118.8 (2×CH), 115.3 (2×CH), 111.9 (2×CH), 64.9 (CH), 55.6 (2×Ch3); LCMS (ES−) 326.2 ([M−H]−, 100%), 255.9 (70), 240.4 (60), 211.4 (70); HRMS (FAB+) Found 327.1226, C17H17N3O4 requires 327.1219; HPLC (CH3CN/H2O, 90:10) tR=1.57 min 99+%); Found: C, 62.10%, H, 5.26%; N, 12.80%, C17H17N3O4 requires: C, 62.38%; H, 5.23%; N, 12.84%.

Provenance & Evidence