Sodium Hydroxide → 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide

Participants

Reaction Conditions

Reaction Steps

Ethyl 5-(3-aminoquinolin-4-ylamino)pentanoate, prepared in Parts A and B of Example 34, was treated as described in Part A of Example 36. Ethoxyacetyl chloride was used instead of methoxypropionyl chloride. Ethyl 5-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (6.0 g, 17 mmol) and ammonium acetate (15 g) were sealed in a high-pressure vessel and heated for four days at 110° C. and then allowed to cool to ambient temperature. Aqueous sodium hydroxide (10%) was added, and the mixture was then extracted with dichloromethane (3×). The product crystallized from the dichloromethane and was collected in two crops to provide 2.64 g of 5-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide as an off-white solid, mp 157-158° C.

Provenance & Evidence