1,2-Dimethoxyethane → HCID 67052447, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol (1.6 g, 4.06 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (0.913 g, 4.87 mmol), potassium carbonate (2.5 g, 18 mmol), dichlorobis(triphenylphosphine)palladium(II)(0.028 g, 0.041 mmol), DME (15 mL), and water (7 mL) was stirred under a nitrogen atmosphere and then heated at 110° C. for 18 hours and allowed to cool to room temperature. An analysis by LC/MS indicated the reaction was incomplete, and additional dichlorobis(triphenylphosphine)palladium(II)(0.050 g) was added. Heating was continued for another six hours, but the reaction did not progress. Additional (4-aminomethylphenyl)boronic acid hydrochloride (0.400 g), potassium carbonate (0.500 g) and dichlorobis(triphenylphosphine)palladium(II)(0.050 g) were added. The reaction was heated at 110° C. for six hours, allowed to cool to room temperature, and concentrated under reduced pressure. Chromatographic purification was carried out as described in Examples 351-365 to provide 1.13 g of 1-[4-amino-7-[4-(aminomethyl)phenyl]-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol as a yellow solid.

Provenance & Evidence