Hydrochloric Acid → HCID 57813269, compound

Participants

Reaction Steps

To a clear solution of 1,1-dimethylethyl [(5-fluoro-3′-formyl-3-biphenylyl)methyl]carbamate (486 mg, 1.48 mmol) in DCM (2 mL) was added 4N HCl in dioxane (1 mL). Solid precipitated out from the solution after 30 min but stirring was continued at RT for another 1 h. The mixture was then concentrated under vacuum to get rid of solvent. The resulting residue was re-dissolved in DCM. Et3N (1.14 mL, 8.20 mmol) was added followed by 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (400 mg, 0.82 mmol) and HBTU (830 mg, 8.20 mmol). The mixture was stirred at RT overnight. The reaction was quenched with saturated NaHCO3 and extracted with DCM twice. The organic layer was then washed with water followed by a brine wash. The organic layer was concentrated under vacuum to give a crude residue. It was purified with CombiFlash chromatography, eluting with 90% ethyl acetate in hexane to obtain N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(5-fluoro-3′-formyl-3-biphenylyl)methyl]-1,3-benzenedicarboxamide (300 mg, 55%). LC-MS m/z 664 (M+H)+

Provenance & Evidence