Ammonium formate → tert-Butyl 3-(8-morpholinoimidazo[1,2-b]pyridazin-2-yl)azetidine-1-carboxylate

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Reaction Conditions

Reaction Steps

Compound 19b (430 mg, 1.09 mmol) and ammonium formate (344 mg, 5.45 mmol) were placed in a 20 mL vial equipped with a stir bar and dissolved in a mixture of THF (8 mL) and MeOH (4 mL). 10% Pd/C (116 mg, 0.109 mmol) was then added. The reaction mixture was stirred at 70° C. for 3 h, cooled to rt, and filtered through a pad of diatomaceous earth. The solids were washed with MeOH (2×10 mL). The combined filtrates were concentrated under reduced pressure and the residue obtained was dissolved in EtOAc (100 mL) and washed with water (2×25 mL) and brine (25 mL). The combined aqueous washings were extracted once with EtOAc (25 mL) and the organic extracts were combined, dried over MgSO4, and filtered. The solvent was removed under reduced pressure to obtain compound 19c. Mass Spectrum (LCMS, ESI pos.): Calcd. for C19H25N5O3: 360.2 (M+H). found: 360.3.

Provenance & Evidence