Sodium Hydroxide → HCID 57731644, compound

Participants

Reaction Steps

2,2-dimethyl-propionic acid 3-(1,3-dihydro-isobenzofuran-1-yl)-5-{3-dimethylcarbamoyl-4-[(morpholine-4-carbonyl)-amino]-phenyl}-pyrrolo[2,3-b]pyridin-1-ylmethyl ester was dissolved in tetrahydrofuran. 1 M sodium hydroxide in methanol was added to the mixture, and the reaction was stirred for 2 hours at room temperature. The reaction was quenched with sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried, filtered, and concentrated. The crude material was purified then by mass-triggered reverse-phase HPLC to afford morpholine-4-carboxylic acid {4-[3-(1,3-dihydro-isobenzofuran-1-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-dimethylcarbamoyl-phenyl}-amide. 1H NMR (250 MHz, DMSO-d6) δ 11.74 (s, 1H), 8.75 (s, 1H), 8.47 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.55-7.49 (m, 3H), 7.44-7.22 (m, 4H), 7.10 (d, J=7.6 Hz, 1H), 6.48 (s, 1H), 5.13 (m, 2H), 3.62-3.58 (m, 4H), 3.42-3.35 (m, 4H in water peak), 2.98 (s, 3H), 2.94 (s, 3H); MS: m/z 512.3 (M+H+).

Provenance & Evidence