Hydrochloric Acid → 3-(6-Methylisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

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Reaction Steps

To a solution of 4-{4-[6-amino-5-(6-methylisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (29.5 mg, 0.0609 mmol) in DCM (1.0 mL, 16 mmol) was added 1.0 M of HCl in Et2O (1.7 mL, 1.7 mmol), and the mixture was stirred at ambient temperature for 6 h. Almost immediately a yellow solid precipitated. The solvents were evaporated, and the residue was transferred into a vial and dried in vacuo overnight to give the title compound as yellow solid. It appeared to be slightly hygroscopic. 1H NMR (400 MHz, DMSO-d6): δ=14.7 (very brs, 1H), 9.41 (s, 1H), 9.26-9.17 (brm, 1H), 9.14-9.02 (brm, 1H), 8.83 (d, J=2.0 Hz, 1H), 8.79 (brs, 1H), 8.62 (s, 1H), 8.51 (s, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.18 (d, J=8.4 Hz, 1H), 8.15 (d, J=0.4 Hz, 1H), 7.87 (s, 1H), 7.66 (dd, J=1.2, 8.4 Hz, 1H), 7.36 (s, 1H), 7.23 (s, 1H), 7.10 (s, 1H), 4.58-4.49 (mc, 1H), 3.40 (brd, J=12.4 Hz, 2H), 3.11 (brq, J=11.8 Hz, 2H), 2.58 (s, 3H), 2.31-2.13 (m, 4H). MS(ES+): m/z=385.20 (38) [MH+], 302.14 (100) [MH+-piperidine]. HPLC: tR=1.78 min (polar—5 min, ZQ2).

Provenance & Evidence