Hydrochloric Acid → HCID 67521376, compound

Participants

Reaction Steps

To a solution of 4-{4-[6-amino-5-(8-chloroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (64.2 mg, 0.127 mmol) in 1,4-dioxane (1.5 mL, 19 mmol) was added HCl (4.0 M in 1,4-dioxane; 1.2 mL, 4.8 mmol), and the mixture was stirred at ambient temperature for 70 min. Almost immediately an off-white solid precipitated. The solid was filtered off, washed with MTBE, and dried in vacuo overnight to give the title compound as yellow solid. It appeared to be slightly hygroscopic during the filtration; however, after the washing and initial drying it appeared to be non-hygroscopic. 1H NMR (400 MHz, DMSO-d6): δ=14.7 (very brs, 1H), 9.68 (s, 1H), 9.23-9.14 (brm, 1H), 9.12-8.99 (brm, 1H), 8.89 (d, J=2.0 Hz, 1H), 8.82 (s, 1H), 8.76 (brs, 2H), 8.52 (s, 1H), 8.49 (d, J=2.0 Hz, 1H), 8.16 (s, 1H), 8.12 (d, J=8.0 Hz, 1H), 7.95 (dd, J=1.2, 7.6 Hz, 1H), 7.90 (t, J=7.8 Hz, 1H), 4.58-4.49 (mc, 1H), 3.40 (brd, J=12.0 Hz, 2H), 3.07 (brq, J=11.2 Hz, 2H), 2.30-2.12 (m, 4H). MS(ES+): m/z=405.13/407.13 (88/60) [MH+], 322.07/324.05 (90/64) [MH+-piperidine]. HPLC: tR=1.98 min (polar—5 min, ZQ3). UV: λmax=210, 244, 352 nm.

Provenance & Evidence