N,N'-Dimethylethylenediamine → 1-[4-amino-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

7-Bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.75 g), 2(1H)-pyridone (0.20 g), copper(I) iodide (68 mg), N,N′-dimethylethylenediamine (75 μL), potassium phosphate (0.79 g) and dioxane (2.7 mL) were added to a scintillation vial. The vial was flushed with nitrogen, sealed with a Teflon-lined cap, placed in an oil bath, and heated to 110° C. for 60 hours. The reaction was cooled to ambient temperature, diluted with chloroform and filtered through a bed of CELITE filter agent. The solvent was evaporated and the residue was purified by column chromatography on a Biotage Horizon™ High-Performance Flash Chromatography instrument using a silica gel cartridge. The purification was carried out eluting with chloroform:CMA in a gradient from 99:1 to 75:25. Additional purification by recrystallization from acetonitrile provided 0.38 g of 1-[4-amino-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinolin-7-yl]-1H-pyridin-2-one as a tan solid, mp 161-163.5° C.

Provenance & Evidence