Acetic Acid → HCID 178488239, compound

Participants

Reaction Steps

Morpholine (0.08 mL, 0.93 mmol) was added into a mixture of N1-{4-[4-amino-1-(4-oxocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide (0.42 g, 0.78 mmol) and acetic acid (0.11 mL, 1.86 mmol) in dichloroethane (25 mL). The mixture was stirred at ambient temperature for 10 minutes. Sodium triacetoxyborohydride (0.23 g, 1.09 mmol) was added and the mixture was stirred at ambient temperature overnight. Water (6 mL) was added followed by sodium bicarbonate (0.38 g, 4.53 mmol). The mixture was stirred for 1 hour and the organic layer was separated. The aqueous layer was extracted with dichloromethane (20 mL). The combine organics were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a crude product. The crude product was purified by flash column chromatography on silica using Isco system to provide cis-N1-{4-[4-amino-1-(4-morpholinocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide (0.23 g, 0.37 mmol) and trans-N1-{4-[4-amino-1-(4-morpholinocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-trifluoromethylbenzamide (0.09 g, 0.14 mmol) as white solids.

Provenance & Evidence