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

Participants

Reaction Steps

The solution of N-(4-methoxybenzyl)-5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.21 g, 0.33 mmol) in CHCl3 (2 mL) and TFA (2 mL) was heated at 80° C. for 12 h. Then the reaction mass was evaporated to dryness and ice cold H2O (10 mL) was added and basified with saturated NaHCO3 solution to pH 8. A white colored solid precipitated out which was collected by filtration and dried under vacuum to give 5-(3-(6-morpholinopyridin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (0.075 g, 44.1%). MS (ESI, pos. ion) m/z: 517 (M+1); 1H NMR (DMSO-d6, 400 MHz): δ ppm 8.94 (s, 1H), 8.51 (s, 1H), 8.14 (d, J=8.8 Hz, 1H), 7.99 (d, J=8.4 Hz, 2H), 7.84 (d, J=8.8 Hz, 1H), 7.68-7.64 (m, 1H), 7.42-7.36 (m, 3H), 7.18 (s, 1H), 6.82 (d, J=8.8 Hz, 1H), 3.77-3.75 (m, 4H), 3.57-3.56 (m, 4H), 2.3 (s, 3H).

Provenance & Evidence