Sodium Iodide → 1,1-Dimethylethyl 4-{[5'-({[(3-{[{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}(methyl)amino]methyl}phenyl)carbonyl]amino}methyl)-2'-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate

Participants

Reaction Steps

To a solution of 1,6-diethyl-5-[(methylamino)methyl]-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (0.0432 g, 0.136 mmol) in DMF (1.0 mL) was added 1,1-dimethylethyl 4-({5′-[({[3-(chloromethyl)phenyl]carbonyl}amino)methyl]-2′-fluoro-3-biphenylyl}methyl)-1-piperazinecarboxylate (0.075 g, 0.136 mmol), and K2CO3 (0.0188 g, 0.136 mmol). This mixture was stirred at room temperature for 18 h after which was added NaI (0.0204 g, 0.136 mmol) and stirring continued for another 25 h. Then the mixture was diluted with EtOAc (5 mL), washed with H2O (2×3 mL), brine (3 mL), concentrated, and purified by CombiFlash chromatograph to afford the title compound 0.055 g (49%). LC-MS m/z 833 (M+H)+.

Provenance & Evidence