Sodium Hydroxide → HCID 68328358, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-(6-(isopropylamino)pyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (200 mg, 0.41 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 H2O (2.0 mL). The precipitate was collected through filtration and the crude product was purified with preparative HPLC (eluent: 10-60% AcCN in H2O with 0.01% TFA) to give 3-(3-(6-(isopropylamino)pyrazin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-amine (40 mg, 24.5%). MS (ESI, pos. ion) m/z: 336.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.96 (s, 1H), 9.07 (s, 1H), 8.25-8.22 (m, 2H), 7.76 (s, 2H), 7.72 (dd, J=6.8, 1.6 Hz, 1H), 7.64 (s, 1H), 7.54 (d, J=8.4 Hz, 1H), 4.30-4.27 (m, 1H), 1.32 (d, J=6.4 Hz, 6H).

Provenance & Evidence