1-Hydroxybenzotriazole → HCID 70984149, compound

Participants

Reaction Steps

To a flask containing 4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)piperidin-4-ol (35 mg, 0.0.082 mmol), EDC (31 mg, 0.0.163 mmol), HOBt (25 mg, 0.163 mmol) and DIEA (0.071 mL, 0.408 mmol) in DMF (1.63 mL) was added 7-quinoline carboxylic acid (42 mg, 0.245 mmol). The solution was stirred at room temperature for 16 hours. The reaction solution was then filtered and purified by mass triggered reverse phase high pressure liquid chromatography to provide 4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)-1-(1H-pyrrolo[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-ol as a white solid. MS ESI calcd. for C30H26F3N7O2 [M+H]+ 574. found 574. 1H NMR (600 MHz, DMSO-d6) δ 11.79 (s, 1H), 10.22 (s, 1H), 9.15 (s, 1H), 8.53 (s, 1H), 8.48 (d, J=5.2 Hz, 1H), 8.45-8.37 (m, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.83-7.79 (m, 1H), 7.54 (s, 1H), 7.47 (s, 1H), 7.31 (s, 1H), 7.25 (d, J=8.0 Hz, 1H), 7.31-7.27 (m, 1H), 6.48 (s, 1H), 4.54-4.43 (m, 2H), 3.30-3.20 (m, 2H), 2.34 (s, 3H), 2.24-2.10 (m, 2H), 1.75-1.68 (m, 1H), 1.60-1.46 (m, 1H). rhSyk IC50=9 nM.

Provenance & Evidence