Piconol → Pyridin-2-ylmethyl{4-[({3-[(tert-butoxycarbonyl)amino]-6-phenylpyridin-2-yl}amino)carbonyl]benzyl}carbamate

Participants

Reaction Steps

Pyridine-2-methanol (0.0345 ml, 0.358 mmol) was added to a 0° C. cooled mixture of CDI (58.0 mg, 0.358 mmol) in THF (5 mL) and the reaction was stirred at room temperature for 1 h. Tert-butyl(2-{[4-(aminomethyl)benzoyl]amino}-6-phenylpyridin-3-yl)carbamate (150 mg, 0.358 mmol) was added to the reaction with TEA (0.050 ml, 0.358 mmol) and DBU (0.054 ml, 0.358 mmol) and the reaction stirred for 2 hours. LC/MS indicated the presence of the addition of the free amine to the CDI and thus another equivalent of pyridine-2-methanol (0.345 ml, 0.358 mmol) was added and the reaction stirred overnight. LC/MS indicated the formation of the desired product. Following evaporation of THF, water was added and the organic product was extracted (3×) with EtOAc, washed with brine and dried over sodium sulfate. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with EtOAc/hexanes (0%-100%). MS: cal'd 554 (MH+), exp 554 (MH+).

Provenance & Evidence