Hydrochloric Acid → 3-(4-Fluoroisoquinolin-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-(4-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (16.0 mg, 0.0327 mmol) in DCM (0.60 mL, 9.4 mmol) was added 1.0 M of HCl in Et2O (0.90 mL, 0.90 mmol), and the mixture was stirred at ambient temperature for 2 h. Almost immediately a pale yellow solid precipitated. The solvents were evaporated, and the residue was transferred into a vial and dried in vacuo overnight, yielding the title compound as pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=14.6 (very brs, 1H), 9.38 (s, 1H), 9.08-8.99 (brm, 1H), 8.91-8.80 (brm, 1H), 8.53 (brs, 1H), 8.46 (d, J=2.0 Hz, 1H), 8.40 (s, 1H), 8.37 (d, J=8.4 Hz, 1H), 8.24 (dd, J=8.2, 0.8 Hz, 1H), 8.06 (d, J=0.4 Hz, 1H), 8.03 (ddd, J=0.8, 7.0, 8.2 Hz, 1H), 7.92 (ddd, J=1.0, 7.0, 8.2 Hz, 1H), 7.88 (brs, 1H), 4.54-4.45 (mc, 1H), 3.38 (brd, J=13.2 Hz, 2H), 3.09 (brq, J=11.6 Hz, 2H), 2.27-2.08 (m, 4H). MS(ES+): m/z=389.18 (18) [MH+], 306.13 (100) [MH+-piperidine]. HPLC: tR=1.69 min (polar—5 min, ZQ2).

Provenance & Evidence