Hydrochloric Acid → 6-phenyl-4-((3S)-3-piperidinylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide

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Reaction Steps

A flask containing (S)-tert-butyl 3-(3-carbamoyl-6-phenylpyrrolo[1,2-b]pyridazin-4-ylamino)piperidine-1-carboxylate (62 mg, 0.142 mmol) was added HCl in dioxane (2 mL, 8 mmol). TLC indicated complete consumption of starting material at 3 h at which time the volatiles were removed via nitrogen sweep and the crude salt was dried under high vacuum to afford the hydrochloride salt of the title compound (58.4 mg, 87% yield) as a yellow solid. A portion of the solids were purified via preparative HPLC (Phenomenex Luna 21.2×100 mm, 1/9 MeOH/H2O to 9/1 MeOH/H2O, 0.1% TFA; 20 mL/min, 10 minute gradient). LCMS: 336.1 (M+H)+; HPLC (conditions E): retention time=5.82 min; 1H NMR (MeOD, 400 MHz) δ 8.21 (s, 1H), 8.05 (d, J=1.8 Hz, 1H), 7.78 (dd, J=1.4, 8.4 Hz, 2H), 7.75 (t, J=7.9 Hz, 2H), 7.26 (m, 2H), 4.68 (m, 1H), 3.73 (dd, J=3.5, 9.0 Hz, 1H), 3.35 (m, 1H), 3.17 (m, 2H), 2.34 (m, 1H), 2.17 (m, 1H), 1.99 (m, 1H), 1.85 (m, 1H).

Provenance & Evidence