Diisopropylethylamine → HCID 68358691, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (((1S,3R)-3-amino-1,2,2-trimethylcyclopentyl)methyl)carbamate (417 mg, 1.626 mmol) and 6-bromo-4-chloropyrrolo[1,2-b]pyridazine-3-carboxamide (446 mg, 1.626 mmol, from preparation 5) in DMF (4.07 ml) was added DIEA (625 μl, 3.58 mmol). The reaction mixture was heated at 90° C. for 2 hrs. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 ml). The ethyl acetate solution was washed with water (3×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding a light yellow oil. The solid was dissolved in 50% EtOAc/hexanes (5 ml) and loaded directly on a pre-packed silica gel column. The crude product was purified via medium pressure chromatography (10-60% EtOAc-hexanes solvent system over 30 minutes) to afford tert-butyl (((1S,3R)-3-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-1,2,2-trimethylcyclopentyl)methyl)carbamate (580 mg, 1.173 mmol, 72.1% yield) as a yellow solid. ESI-MS m/z 496.1 ([M+H]+).

Provenance & Evidence