Sodium Hydroxide → 3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-N-isopropyl-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-isopropyl-1,2,4-oxadiazol-5-amine (200 mg, 0.375 mmol) in 1,4-dioxane (2.0 mL) was added 10% aq NaOH (1.0 mL) and the reaction was heated at 100° C. for 2 h. The mixture was cooled to RT and treated with ice cold water (2.0 mL). The precipitate was collected through filtration and the crude product was purified with preparative HPLC (eluent: 60-90% MeCN in water with 0.01% TFA) to give 3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-N-isopropyl-1,2,4-oxadiazol-5-amine (40 mg, 28.0%). MS (ESI, pos. ion) m/z: 379.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.96 (s, 1H), 9.11 (s, 1H), 8.73 (s, 1H), 8.34 (d, J=2.0 Hz, 1H), 8.24 (d, J=7.6 Hz, 1H), 7.93 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 5.55-5.49 (m, 1H), 3.93-3.85 (m, 1H), 1.47 (d, J=6.0 Hz, 6H), 1.25 (d, J=6.4 Hz, 6H).

Provenance & Evidence