Trifluoroacetic acid → HCID 178480246, compound

Participants

Reaction Conditions

Reaction Steps

A 50 mL round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-(1-methylpiperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (16.3 mg, 0.0241 mmol) and CF3COOH (5 mL). The reaction mixture was stirred at 80° C. overnight. The solvent was removed and the residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to afford product, which was further purified by preparative HPLC to afford the desired product (3.2 mg, 16.9%). LRMS (APCI pos): >99% purity, 254 nm, m/e 558 (M+1). 1H NMR (400 MHz, CD3OD) δ 11.94 (s, 1H), 8.24-8.36 (m, 3H), 8.03 (dd, 1H), 7.65 (m, 2H), 7.49 (m, 1H), 7.41 (m, 1H), 7.22-7.30 (m, 2H), 6.31 (d, 1H), 3.62 (m, 2H), 3.45 (m, 1H), 3.14-3.26 (m, 2H), 2.87 (s, 3H), 2.39-2.58 (m, 2H), 2.14-2.32 (m, 2H).

Provenance & Evidence