Trifluoroacetic acid → HCID 59304262, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with tert-butyl 1-(1-(4-methoxybenzyl)-4-(2-fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)piperidin-4-yl(methyl)carbamate (98.5 mg, 0.124 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 give the product, which was not pure enough. The impure product was further purified by preparative HPLC to afford product (17.3 mg, 24.3%). LRMS (APCI pos) m/e 573 (M+1). 1H NMR (400 MHz, CD3OD δ 11.97 (s, 1H), 8.38 (d, 1H), 8.33 (d, 1H), 8.25 (d, 1H), 8.08 (m, 1H), 7.65 (m, 2H), 7.48 (d, 1H), 7.40 (m, 1H), 7.28 (m, 2H), 6.28 (d, 1H), 4.10 (m, 2H), 3.32 (m, 1H), 3.01 (m, 2H), 2.72 (s, 3H), 2.18 (m, 2H), 2.81 (m, 2H).

Provenance & Evidence