Sodium Hydroxide → HCID 68327959, compound

Participants

Reaction Steps

To a solution of 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1-tosyl-1H-indol-3-yl)-N-methylnicotinamide (150 mg, 0.283 mmol) in 1,4-dioxane (3 mL) was added aq.NaOH (7 M, 3 mL) and the reaction was heated at 90° C. for 1 h. The reaction was then quenched with water to get a precipitate. The precipitate was filtered and washed with water (2×100 mL) and dried. The crude product was purified with preparative HPLC (eluting with 30-70% MeCN in water with 0.1% TFA in each solvent) to give 5-(5-(5-(isopropylamino)-1,3,4-oxadiazol-2-yl)-1H-indol-3-yl)-N-methylnicotinamide (30 mg, 28%). MS (ESI, pos. ion) m/z: 377.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 11.95 (s, 1H), 9.04 (d, 1H, J=2.0 Hz), 8.89 (d, 1H, J=2.0 Hz), 8.74-8.76 (m, 1H), 8.44-8.45 (m, 1H), 8.24 (s, 1H), 8.02 (d, 1H, J=2.0 Hz), 7.73 (dd, 1H, J=8.8, 2.0 Hz), 7.62-7.66 (m, 2H), 3.71-3.76 (m, 1H), 2.85 (d, 3H, J=4.4 Hz), 1.22 (d, 6H, J=6.4 Hz).

Provenance & Evidence