4-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole → 4-[(3-Hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

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Reaction Steps

To a solution of 4-[(3-Benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (0.4 g, 1.05 mmol) in anhydrous THF/MeOH (20 mL) was added Pd—C (10% by wt., 0.04 g). The black suspension was then stirred under an atmosphere of hydrogen (balloon) for 16 h. The catalyst was removed by filteration through Celite® and exhaustively washed with THF. The filtrate was concentrated in vacuo to give a beige residue. Recrystallisation from EtOH gave STX333 as a colourless solid (0.27 g, 88%) after recrystallisation; δH (400 MHz, DMSO-d6) 4.97 (s, 2H), 6.68 (AA′BB′, 2H), 6.72-6.75 (m, 3H), 7.11 (m, 1H), 7.76 (AA′BB′, 2H), 8.77 (s, 2H), 9.49 (br s, 1H—exchanges with D2O); LRMS (FAB+) m/z (rel. intensity) 292 (100%, [M+H]), 223 (42, [M+H-triazole]); HPLC tR=2.22 min, (96%); HRMS (FAB+) Found 292.1198; C16H13N5O requires 292.1192;

Provenance & Evidence