Sodium Hydroxide → HCID 68328330, compound

Participants

Reaction Steps

To a solution of N-(3-(3-(6-isopropoxypyrazin-2-yl)-1-tosyl-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl)acetamide (220 mg, 0.47 mmol) in 1,4-dioxane (2.0 mL) was added 10% aq NaOH (1.0 mL) and the reaction was stirred at RT for 48 h. The mixture was treated with ice cold water (5.0 mL) and the precipitate was filtered and washed with water. The crude product was purified with preparative HPLC (eluent: 50-80% MeCN in water with 0.01% TFA) to give N-(3-(3-(6-isopropoxypyrazin-2-yl)-1H-indol-5-yl)-1,2,4-oxadiazol-5-yl)acetamide (10 mg, 5.6%). MS (ESI, pos. ion) m/z: 379.2 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 12.10 (brs, 2H), 9.17 (s, 1H), 8.74 (s, 1H), 8.42 (d, J=2.4 Hz, 1H), 7.96 (s, 1H), 7.82 (dd, J=8.4, 1.2 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 5.53-5.47 (m, 1H), 2.23 (s, 3H), 1.51 (d, J=6.4 Hz, 6H).

Provenance & Evidence