Sodium Methoxide → 4-[(4-Chloro-3-hydroxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Participants

Reaction Steps

A solution of 4-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole (1.13 g, 2.63 mmol) and NaOMe (500 mg) in MeOH (20 mL) and water (5 mL) was heated to reflux for 30 minutes. After cooling to room temperature most of the solvent was removed in vacuo and concentrated sodium bicarbonate solution (20 mL) and EtOAc (50 mL) were added. The organic layer was separated, dried (Na2SO4) and the solvent was removed under reduced pressure. The resulting white powder was refluxed in EtOAc (10 mL, product did not dissolve completely). The product was filtered off and dried in vacuo to give STX483 as a white powder (0.412 g, 48%); δH (400 MHz, DMSO-d6) 4.97 (s, 2H), 6.71-6.75 (m, 3H, AA′BB′ and ArH), 6.84 (d, J=2.0, 1H), 7.25 (d, J=8.2, 1H), 7.75 (AA′BB′, 2H), 8.76 (s, 2H), 10.21 (s, 1H—exchanges with D2O); LRMS (FAB+) m/z (rel. intensity) 326.1 (100, [M+H]+).

Provenance & Evidence