Sodium Hydroxide → 3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (160 mg, 0.32 mmol) in 1,4-dioxane (1.6 mL) was added 10% aq NaOH (0.8 mL) and the reaction was heated at 100° C. for 2 h. The mixture was cooled to RT and treated with ice cold water (1.5 mL). The precipitate was collected through filtration and the crude product was purified with preparative HPLC (eluent: 20-70% AcCN in H2O with 0.01% TFA) to give 3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-N-methyl-1,2,4-oxadiazol-5-amine (23 mg, 20.7%). MS (ESI, pos. ion) m/z: 351.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.96 (s, 1H), 9.15 (s, 1H), 8.74 (s, 1H), 8.38 (d, J=1.6 Hz, 1H), 8.18 (dd, J=8.8, 4.4 Hz, 1H), 7.94 (s, 1H), 7.77 (dd, J=8.4, 1.2 Hz, 1H), 7.55 (d, J=8.8 Hz, 1H), 5.56-5.53 (m, 1H), 2.96 (d, J=4.0 Hz, 3H), 1.49 (d, J=6.0 Hz, 6H).

Provenance & Evidence