Acetic Acid → HCID 118131401, compound

Participants

Reaction Steps

3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(1,2,3,6-tetrahydropyridin-4-yl)-1H-isochromen-1-one hydrochloride (example 64, 37 mg, 0.064 mmol), isonicotinaldehyde (8.89 mg, 0.083 mmol) and DIEA (11.15 μl, 0.064 mmol) were dissolved in DCM (1.23 ml) followed by a spatula tip of anhydrous Na2SO4, and the mixture stirred rt for 10 min prior to add AcOH (10.97 μl, 0.192 mmol) and NaBH(OAc)3 (27.1 mg, 0.128 mmol). The resulting mixture was stirred for 1 h at rt, then quenched with 2M HClaqueous (1 ml), filtered to remove insoluble materials, and the filtrate purified via reverse phase chromatography using a Biotage C18 60 g SNAP with a gradient of water and acetonitrile to give (prior to drying a small amount of 1M HClaqueous was added) the title compound (10.6 mg, 26.5%) as white solid.

Provenance & Evidence