Water → (S)-tert-butyl 3-(6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-ylamino)piperidine-1-carboxylate

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Reaction Conditions

Reaction Steps

A solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 171 mg, 0.62 mmol) and (S)-tert-butyl 3-aminopiperidine-1-carboxylate (125 mg, 0.62 mmol) in DMF (4 mL) was added DIPEA (0.326 mL, 1.87 mmol). The mixture was heated at 80° C. for 18 h then cooled to rt. Water (16 mL) was added and the resulting suspension was stirred for 1 h. The solids were filtered, rinsed with water (2×), and then dried to afford the crude product which was purified via silica gel chromatography (10% to 50% ethyl acetate in hexanes) to afford the title compound (175 mg, 64% yield) as a pale yellow solid. 1H NMR (DMSO-d6, 400 MHz) δ 10.89 (br s, 1H), 8.26 (s, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.00 (br m, 2H), 4.18 (s, 1H), 3.68 (m, 1H), 3.35 (m, 3H), 1.99 (m, 1H), 1.70 M, 1H), 1.57 (m, 1H), 1.23 br s, 9H).

Provenance & Evidence