Hydrochloric Acid → 4-(4-Aminopyrazolo[4,3-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(2,6-dichloro-4-cyano-phenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]carbamic acid tert-butyl ester (5.0 g, contaminated with residual tert-butyl carbamate) and HCl (4 N in dioxane, 40 mL, 160 mmol) was stirred at 50° C. for 6 h then concentrated to dryness under reduced pressure. The resultant residue was partitioned between ethyl acetate and sodium bicarbonate (sat. aq.). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (1.17 g, 39% yield over 2 steps). 1H NMR (400 MHz, CDCl3): δ 8.95 (s, 1H), 8.48 (s, 2H), 7.58 (d, J=6.9 Hz, 1H), 7.27-7.22 (m, 1H), 7.19-7.14 (m, 1H), 6.91-6.88 (m, 1H). LCMS (Method D): RT=1.95 min, m/z: 304 [M+H+].

Provenance & Evidence