Trifluoroacetic acid → 2-(3-fluoro-4-(3-(1-methylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenylamino)-N-(4-fluorophenyl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

A 25 mL round-bottomed flask was charged with 2-(4-(1-(4-methoxybenzyl)-3-(1-methylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenylamino)-N-(4-fluorophenyl)nicotinamide (0.023 g, 0.0333 mmol) and TFA (3 mL). The reaction mixture was heated to 70° C. for 1 hour. The reaction was concentrated and the residue was purified by preparative TLC [0.5 mm thickness eluting with 15% MeOH(NH3)/CHCl3] to provide the product (9 mg, 46%). LRMS M−1 (571.1) observed. 1H NMR (400 MHz, CDCl3) δ 10.56 (s, 1H), 10.12 (br s, 1H), 8.43 (m, 1H), 8.18 (m, 1H), 8.06 (m, 2H), 7.91 (m, 1H), 7.53 (m, 2H), 7.31 (m, 1H), 7.13 (m, 3H), 6.86 (m, 1H), 6.11 (m, 1H), 4.58 (d, J=7 Hz, 1H), 3.74 (br s, 1H), 2.92 (br s, 2H), 2.37 (s, 3H), 2.27 (br s, 2H), 1.72 (br s, 2H), 1.59 (br s, 1H). 19F NMR (376 MHz, CDCl3) δ −76.0 (3F), −117.0 (1F), −127.6 (1F).

Provenance & Evidence