4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid → N-(3-fluoro-4-(3-(1-isopropylpiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxamide

Participants

Reaction Steps

Prepared by a 2-step process from 4-(4-amino-2-fluorophenoxy) N-(1-isopropylpiperidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (prepared as described in Example 101, Step A except using 1-isopropylpiperidin-4-amine) and 4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid (Example 125, Step E) according to the procedure of Example 101, Step B. The crude was rinsed with Et2O to afford 4.6 mg (64%) of the desired product. The desired product was treated with 2N HCl (Et2O solution) in a solution of MeOH and EtOAc to afford HCl salt compound. LRMS (APCIpos) m/e 601.3 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.17 (d, 1H), 8.06 (dd, 1H), 7.91 (d, 1H), 7.84 (d, 1H), 7.55 (m, 2H), 7.49 (d, 1H), 7.34 (t, 3H), 6.14 (d, 1H), 3.93 (m, 1H), 3.52 (m, 2H), 3.17 (m, 2H), 2.47 (m, 2H), 1.96 (m, 2H), 1.40 (d, 6H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −111.0, −127.6.

Provenance & Evidence