Isopropylamine → 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-(4-chloropyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (500 mg, 0.85 mmol) in DMSO (5 mL) was added isopropylamine (60 mg, 1.02 mmol). The mixture was stirred at 110° C. for 12 h. The reaction was quenched with ice cold H2O and was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified with flash chromatography (basic alumina, eluting with 30-40% EtOAc in Hex) to give 5-(3-(4-(isopropylamino)pyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine (220 mg, 52%). MS (ESI, pos. ion) m/z: 609.6 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 9.07 (s, 1H), 8.39 (s, 1H), 8.23 (m, 1H), 8.12 (d, J=8 Hz, 1H), 8.00 (d, J=8 Hz, 2H), 7.85 (d, J=8.4 Hz, 1H), 7.79-7.57 (m, 5H), 7.43 (d, J=8 Hz, 2H), 7.312 (d, J=8 Hz, 3H), 6.90 (d, J=8 Hz, 2H), 4.38 (m, 3H), 3.72 (s, 3H), 2.32 (s, 3H), 1.17 (d, J=6.4 Hz, 6H).

Provenance & Evidence