3-(4-Fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride → 3-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

Participants

Reaction Steps

The procedure for the preparation of 3-(4-fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride was followed, except using 4-{4-[6-amino-5-(5-chloro-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester in place of 4-{4-[6-amino-5-(4-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester. This afforded the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.11-2.28 (m, 4H), 3.01-3.17 (m, 2H), 3.32-3.47 (m, 2H), 4.47-4.60 (m, 1H), 7.66 (dd, J=9.85, 8.59 Hz, 1H), 8.08-8.15 (m, 2H), 8.34-8.51 (m, 3H), 8.56 (s, 1H), 8.77 (d, J=2.02 Hz, 1H), 9.00 (br. s., 1H), 9.16 (br. s., 1H), 9.67 (s, 1H). 1H NMR (400 MHz, CD3OD): δ=2.29-2.44 (m, 4H), 3.20-3.30 (m, 2H), 3.60 (d, J=12.6 Hz, 2H), 4.54-4.66 (m, 1H), 7.39 (t, J=9.1 Hz, 1H), 7.91 (dd, J=8.3, 4.8 Hz, 1H), 7.94 (s, 1H), 8.14 (s, 1H), 8.18 (s, 1H), 8.29 (s, 1H), 8.43 (s, 1H), 9.61 (s, 1H). MS (ES+): m/z=339.76/341.64 [MH+]. HPLC: tR=2.27 min (ZQ2, polar—5 min).

Provenance & Evidence