Imidazole → Methyl (S)-2-(3-(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate

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To a solution of 3-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine (0.1 g, 0.16 mmol) in anhydrous 1,4-dioxane (3 mL) was added CDI (0.13 g, 0.79 mmol) followed by the addition of imidazole (0.05 g, 0.78 mmol) and the contents were stirred at ambient temperature. After 16 h, DIPEA (0.12 mL, 0.64 mmol) and (S)-methyl-2-amino-2-phenylacetate (0.064 g, 0.32 mmol) were added and stirred. After 2 h, the reaction mixture was quenched with H2O and the organic contents were extracted with EtOAc (2×20 mL), dried over anhydrous Na2SO4 and concentrated. The residue thus obtained was purified by preparative HPLC to afford the title compound MS ES calc'd. for C51H46N6O5 [M+H]+ 823. Found 823.

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