Trifluoroacetic acid → HCID 57813477, compound

Participants

Reaction Steps

To 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (30 mg, 0.066 mmol) was added 1,1-dimethylethyl (2S)-4-({3-[4-(aminomethyl)-2-pyridinyl]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (26.3 mg, 0.066 mmol) followed by HBTU (30.2 mg, 0.080 mmol) and TEA (18.52 μl, 0.133 mmol) in dichloromethane (DCM) (664 μl) to give a reaction mixture that was stirred at room temperature overnight. Then the reaction was quenched by H2O (1 drop) and the solvent was removed by Glas-Col. The crude product was redissolved in MeOH/DMSO and purified using a Gilson HPLC (acidic conditions), concentrated by GeneVav EZ-2 evaporator. To this product was added TFA (102 μl, 1.329 mmol) in dichloromethane (0.2 mL) then stirred at room temperature overnight. The reaction mixture was dissolved in MeOH/DMSO and purified using a Gilson HPLC (acidic conditions), concentrated by GeneVav EZ-2 evaporator and basified with an amine cartridge to afford 16.6 mg (33%) of the title compound. LC-MS m/z 730 (M+H)+.

Provenance & Evidence