Triethylamine → N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)propanediamide

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Reaction Steps

A mixture of 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid (77 mg, 0.198 mmol), (({3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amine (64.1 mg, 0.218 mmol), HATU (90 mg, 0.238 mmol), triethylamine (0.080 mL, 0.574 mmol) and dichloromethane (DCM) (3 mL) was stirred overnight at room temperature. The reaction was diluted with EtOAc; washed in turn with saturated aqueous NaHCO3, then saturated aqueous NaCl. The organic phase was dried (Na2SO4) and evaporated to a residue (185 mg). The residue was purified on a Gilson HPLC on RP column using a CH3CN—H2O (0.1% TFA) gradient [10-80%]. Fractions containing the desired product were combined and reduced to a small volume, and then treated with saturated aqueous NaHCO3. The mixture was extracted with EtOAc (2×); the combined extracts were washed with saturated aqueous NaCl and dried (Na2SO4), then solvent was evaporated of to give a glassy solid (61.6 mg). LC-MS m/z 666.6 (M+H)+, 0.75 min (ret time).

Provenance & Evidence