Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-[(3-Bromo-2-methylphenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

Participants

Reaction Steps

3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (918 mg, 0.002 mol) and [(3-bromo-2-methylphenyl)methyl]amine hydrochloride (521 mg, 0.0022 mol) in DCM (25 mL) was treated with HATU (912 mg, 0.0024 mol) followed by TEA (0.404 g, 0.56 mL, 0.004 mol). The reaction was stirred overnight at room temperature. LC-MS showed that the reaction was complete. The reaction was quenched with sat. aq. NaHCO3. The aqueous phase was re-extracted with DCM (2×). Combined organic extracts were washed with H2O, then sat. aq. NaCl and dried (Na2SO4), then concentrated to give a residue (1.4 g). This was purified on the ‘CombiFlash’ using 40 g silica gel column [DCM-MeOH, 0-10%]. This afforded the title compound as a glassy, pale yellow foam [1.35 g (Quant.)]. LC-MS m/z 634.7 (M+H)+.

Provenance & Evidence