Trifluoroacetic acid → HCID 44193619, compound

Participants

Reaction Steps

To 6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid (50 mg, 0.110 mmol) was added 1,1-dimethylethyl 4-({3-[4-(aminomethyl)-2-pyridinyl]phenyl}methyl)-1-piperidinecarboxylate (42.2 mg, 0.110 mmol) followed by HBTU (50.3 mg, 0.133 mmol) and TEA (30.8 μl, 0.221 mmol) in dichloromethane (DCM) (1105 μL) to give a reaction mixture. This was stirred at room temperature overnight. Then the reaction was quenched with H2O (1 drop) and the solvent was removed by Glas-Col. The crude product was redissolved in MeOH/DMSO (1/1) and purified using a Gilson HPLC (acidic condition). Product-containing fractions were combined and evaporated by GeneVac EZ-2 evaporator. To this residue was added TFA (0.170 mL, 2.21 mmol) in dichloromethane (0.2 mL) and the mixture was placed in the Glas-Col evaporator overnight. Then it was redissolved in MeOH/DMSO and purified using a Gilson HPLC (acidic condition). Product-containing fractions were combined and evaporated by GeneVac EZ-2 evaporator, basified by cartridge to afford 25.4 mg (31%) of the title compound. LC-MS m/z 716 (M+H)+.

Provenance & Evidence