Acetic Acid → HCID 68291228, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (Intermediate 2, 334 mg, 1.217 mmol) and (3R,4R)-tert-butyl 4-amino-3-ethylpiperidine-1-carboxylate (1.2 eq., Intermediate 8), AcOH (351 mg, 1.217 mmol) in DMF (3.0 ml) was added DIEA (1275 μl, 7.30 mmol). The reaction was heated at 90° C. for 5 hrs. The reaction was diluted with ethyl acetate (100 ml), and washed with water (3×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified via medium pressure chromatography (silica gel column, EtOAc/hexanes eluent, 0-100% gradient elution) to afford (3R,4R)-tert-butyl 4-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-3-ethylpiperidine-1-carboxylate (428.4 mg, 0.919 mmol, 75.0% yield) as a faint yellow solid. LCMS (Method K) m/z 468.2 ([M+H]+).

Provenance & Evidence