Hydrochloric Acid → HCID 178461055, compound

Participants

Reaction Steps

1N HCl (1.0 mL) was added to a solution of N-(3-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.050 g, 0.083 mmol) in THF/MeOH (2:1, 3 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate (50 mL) and saturated NaHCO3 (50 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with ethyl acetate to give N-(3-(3-(2,3-dihydroxypropoxy)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.008 g, 17%) as a solid. 1H NMR (400 MHz, CD3OD) δ 9.0 (s, 1H), 8.7 (s, 1H), 7.7 (m, 1H), 7.6-7.4 (m, 3H), 7.1 (m, 1H), 7.0 (m, 1H), 4.2 (m, 1H), 4.1-4.0 (m, 3H), 3.7 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=560.1.

Provenance & Evidence