Morpholine → N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

The solution of 5-(3-(6-chloropyridin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (1.0 g, 1.70 mmol) and morpholine (0.178 g, 2.05 mmol) was taken in sealed tube and heated at 130° C. for 5 h, then cooled to RT and poured in cooled ice water (5 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried, filtered and concentrated to give N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.52 g, 48%) as an off-white solid. MS (ESI, pos. ion) m/z: 637 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.95 (s, 1H), 8.51 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.99 (d, J=8.4 Hz, 2H), 7.85-7.82 (m, 1H), 7.72-7.64 (m, 2H), 7.42-7.39 (m, 3H), 7.32 (d, J=8.4 Hz, 2H), 6.9 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.8 Hz, 1H), 4.3 (s, 2H), 3.75 (m, 8H), 3.56 (s, 3H), 2.31 (s, 3H).

Provenance & Evidence