Diisopropylethylamine → Benzyl 2-(4-(4-(5-((5-(tert-butyl)oxazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Participants

Reaction Steps

To a solution of benzyl 2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (150 mg, 0.350 mmol) in DCM (6 ml) at room temperature was added 1,1′-thiocarbonyldi-2(1H)-pyridone (85 mg, 0.368 mmol) and the reaction was stirred at room temperature for 0.5 hr. To the mixture was added 1-amino-3,3-dimethylbutan-2-one (80 mg, 0.525 mmol) and DIPEA (0.110 ml, 0.630 mmol) and the mixture was stirred at 40° C. or until the reaction was completed. To the mixture was added EDC.HCl (268 mg, 1.400 mmol) and the reaction was stirred at 40° C. overnight. The reaction mixture was concentrated and purified by flash chromatography (10 to 50% EtOAc/Heptane) to give the title compound (100 mg, 51.8% yield). LC/MS, ESI-MS(+) m/z 552.1, RT: 1.73 (Condition R).

Provenance & Evidence