Ethyl bromoacetate → Ethyl N-[2-({2-[4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1-piperidinyl]ethyl}amino)-6-(methyloxy)-3-pyridinyl]glycinate

Participants

Reaction Steps

A mixture of 1,1-dimethylethyl [1-(2-{[3-amino-6-(methyloxy)-2-pyridinyl]amino}ethyl)-4-piperidinyl]carbamate (2.8 g, 7.6 mmol), ethyl bromoacetate (0.85 ml, 1.3 g, 7.6 mmol) and potassium carbonate (2 g, 15.2 mmol) in acetonitrile (40 ml) and DMF (20 ml) was stirred under argon overnight. The mixture was filtered, washing with acetonitrile, and evaporated. The residue was dissolved in the minimum volume of DCM (20 ml) and washed with water (20 ml). The organic extract was added to a silica column which was then eluted with 0-100% ethyl acetate in hexane affording a brown oil (1.3 g, 38%).

Provenance & Evidence