4-Toluenesulfonyl chloride → HCID 16742453, compound

Participants

Reaction Steps

To a stirred solution of 1H-imidazo[4,5-c][1,5]naphthyridine (4.5 g, 14.8 mmol) in dichloroethane (100 mL) was added 3-chloroperoxybenzoic acid (mCPBA) (77%, 4.9 g, 22.2 mmol), and the reaction was stirred at room temperature for 2 hours. To the reaction was then added ammonium hydroxide (100 mL) followed by p-toluenesulfonyl chloride (3.4 g, 17.7 mmol), and the reaction was stirred for 5 days at room temperature. To the reaction was added water and the reaction was transferred to a separatory funnel. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, dried (MgSO4), filtered, and evaporated to afford an orange solid. The product was purified by preparative HPLC (Analogix Separation System, and eluted with a gradient of 0-10% methanol in dichloromethane with 1% ammonium hydroxide) to provide a solid which was triturated with acetonitrile and filtered. The residue was washed with acetonitrile and then with ether and dried in a vacuum oven to afford 1-benzyl-2-ethoxy-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine (2.0 g) as a white solid.

Provenance & Evidence