Trifluoroacetic acid → HCID 59304290, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of N-(4-(1-(4-methoxybenzyl)-3-(1-methylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-3-oxo-2-(pyridin-2-yl)-2,3-dihydropyridazine-4-carboxamide (0.014 g, 0.02072 mmol) and 2,2,2-trifluoroacetic acid (TFA) (0.1596 ml, 2.072 mmol) was heated to 60° C. for 18 hours under N2. The mixture was concentrated in vacuo using toluene (3×5 mL) to azeotrope residual TFA. The residue was partitioned between saturated aqueous NaHCO3 and EtOAc. The phases were separated, and the organic phase washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was triturated with ether and decanted to obtain the product as a brown powder (10 mg, 86%). LRMS (apci pos): >99% purity, 220 nm, m/z 556 (M+H); 1H NMR (400 MHz, CDCl3) δ 11.77 (s, 1H), 8.74 (m, 1H), 7.44 (d, 1H), 8.28 (d, 1H), 8.02 (m, 2H), 7.66 (d, 1H), 7.53 (t, 1H), 7.42 (m, 1H), 7.24 (m, 1H), 6.10 (br s, 1H), 4.55 (bd, 1H), 3.80 (br s, 1H), 3.16 (br s, 2H), 2.44 (m, 10H); 19F NMR (376 MHz, CDCl3) δ −125.2 (m).

Provenance & Evidence