1-Hydroxybenzotriazole → HCID 24801479, compound

Participants

Reaction Steps

A mixture of 0.04 g (0.083 mmol) 4-[2-(3,4,5-trimethoxy-phenylamino)-benzooxazol-7-yl]-thiophene-2-carboxylic acid, 0.025 g (0.127 mmol) EDC-HCl, 0.016 g (0.128 mmol) DMAP, 0.83 ml (1.7 mmol) methylamine THF solution (2M), 0.012 g (0.088 mmol) HOBt and 4 ml dichloromethane is stirred at room temperature for 72 h. Then EtOAc is added to the reaction mixture and the organic layer is washed with water (2×), dried over MgSO4, filtered and the filtrate is concentrated in vacuo. The residue is purified by chromatography (silicagel, hexane:EtOAc=1:2), followed by crystallization from dichloromethane/diethyl ether to afford the title compound as off-white crystals. Rt=2.15 min (Waters Symmetry C8, 2.1×50 mm, detection 210-250 nM, 5% to 100% CH3CN in H2O in 2 min+0.05% TFA, flow rate 1.0 ml/min); MS: 440 (M+1)+; m.p. 260-262° C.

Provenance & Evidence