N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → N-[[4-(N,N-diethylaminomethyl)-2-fluoropyridin-3-yl]methyl]-6-iodoquinoxaline-2-carboxamide

Participants

Reaction Steps

This compound was prepared, starting from compounds 90 (0.70 g, 3.31 mmol) and 9 (1.09 g, 3.31 mmol), according to the procedure developed for compound 10. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 99/1, v/v) to give compound 91 (926 mg, 1.88 mmol) as a beige solid. Yield 57%; Rf (Al2O3, CH2Cl2/EtOH, 99/1, v/v) 0.38; mp 147-149° C.; IR (KBr) ν 1160, 1413, 1477, 1508, 1679, 2967 cm−1; 1H NMR (400 MHz, CDCl3) δ 1.13 (t, 6H, J=7.1 Hz), 2.66 (m, 4H), 3.80 (se, 2H), 4.82 (d, 2H, J=6.0 Hz), 7.19 (m, 1H), 7.71 (d, 1H, J=8.8 Hz), 8.02 (dd, 1H, J=1.8, 8.8 Hz), 8.08 (d, 1H, J=4.8 Hz), 8.55 (d, 1H, J=1.8 Hz), 9.14 (m, 1H), 9.61 (s, 1H); ESI-MS m/z 493.9 [M+H]+.

Provenance & Evidence