ZM 241385

51-67-2

139181-28-5

139180-30-6

A reaction was carried out in acetonitrile (25 mL) with p-hydroxyphenethylamine (tyramine, 490 mg, 3.75 mmol) and 2-(furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amine (250 mg, 892 μmol). The reaction mixture was stirred at room temperature for 22 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was adsorbed through diatomaceous earth and purified using column chromatography (eluent: dichloromethane/methanol, 25:75, v/v). The target product grade was collected, evaporated to dryness and subsequently recrystallized from ethyl acetate to afford 4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino)ethyl)phenol (100 mg, 33% yield) as a white solid, melting point: 229-231 °C (literature value: 225- 227°C). The product was analyzed and confirmed by 1H NMR, 13C NMR, high resolution mass spectrometry (HRMS) and high performance liquid chromatography (HPLC).1H NMR (400 MHz, d6-DMSO, 353 K) δ 8.91 (s, 1H), 7.92 (br s, 2H), 7.79 (m, 1H), 7.14 (br t, 1H), 7.04 (m, 3H) , 6.71 (m, 2H), 6.64 (dd, J = 3.3, 1.8 Hz, 1H), 3.49 (m, 2H), 2.78 (m, 2H).13C NMR (101 MHz, d6-DMSO) δ 161.1 (C), 159.0 (C), 155.9 (C), 155.4 (C), 150.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C), 146.1 (C). 146.1 (C), 144.1 (CH), 129.1 (CH), 115.0 (CH), 111.4 (CH), 111.2 (CH), 42.4 (CH2), 33.9 (CH2). HRMS (C16H15N7O2): Calculated value 338.1360 [M + H]+, measured value 338.1353. HPLC : tR 7.34 min, purity 98% (214 nm), 97% (254 nm).