Trifluoroacetic acid → HCID 67089008, compound

Participants

Reaction Steps

A mixture of tert-butyl 5-(6-chloro-2-fluoro-3-(propylsulfonamido)benzamido)-3-ethoxy-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.090 g, 0.162 mmol) and TFA (3.12 mL, 40.5 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure using toluene to azeotrope. The crude material was purified by silica gel flash column chromatography (5% 7N NH3-MeOH in CH2Cl2) to afford 6-chloro-N-(3-ethoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-2-fluoro-3-(propylsulfonamido)benzamide (40 mg, 54% yield). LRMS (ACPI pos) m/e 456.1 (M+1). 1H NMR (400 MHz, d6-DMSO) δ 12.57 (s, 1H), 11.08 (s, 1H), 9.98 (br s, 1H), 8.55 (d, 1H), 8.50 (d, 1H), 7.55 (t, 1H), 7.46 (d, 1H), 4.40 (q, 2H), 3.16 (t, 2H), 1.75 (m, 2H), 1.42 (t, 3H), 0.99 (t, 3H); 19F NMR (376 MHz, DMSO) δ−124.0.

Provenance & Evidence