Acetic Acid → HCID 118131363, compound

Participants

Reaction Steps

To a solution of 3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,5,6-tetrahydropyridin-3-yl)-1H-isochromen-1-one formate (example 171, 0.03 g, 0.055 mmol), 1-methylpiperidin-4-one (0.08 ml, 0.066 mmol) and DIPEA (0.009 ml, 0.055 mmol) in DCM (2 ml) dry Na2SO4 was added and the mixture stirred at RT for 10 min. AcOH (0.009 ml, 0.165 mmol) and sodium triacetoxyborohydride (0.023 g, 0.11 mmol) were added in this order and the reaction mixture was stirred for 3 hrs at RT. The reaction was quenched by the addition of 2M HCl (2 ml), the mixture was filtered and the filtrate was purified by reverse phase flash chromatography on Biotage C18 cartridge (water/MeCN 90/10+0.1% HCOOH to water/MeCN 5/95+0.01% HCOOH). Before drying 2M HCl (2 ml) was added and the mixture was dried under reduced pressure to afford title compound (0.025 g, 0.037 mmol, 68%).

Provenance & Evidence