Hydrochloric Acid → HCID 46940346, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-N—((S)-1-((R)-pyrrolidin-3-yl)ethyl)ethanamine (0.14 g, 0.87 mmol) and diisopropylethylamine (0.38 mL, 2.18 mmol) are added to a mixture of 9-cyclopropyl-6,7-difluoro-3-hydroxyl-8-methoxy-4-oxo-4,9-dihydrothieno[2,3-b]quinoline-2-carbonitrile (0.15 g, 0.44 mmol) in DMSO (2 mL). The reaction mixture is heated at 110° C. for 18 h, and cooled to rt. The resulting solution is purified by preparative HPLC using mass-based fraction collection to provide the desired mass only fractions. The fractions containing product were combined and lyophilized. The resulting solid was treated with a solution of 1.25 M HCl in methanol (3 mL), evaporated, and triturated with diethyl ether. This step was repeated three times. The brown solid was dissolved in water and lyophilized to afford the desired product (66.1 mg, 29%, HCl salt) as a brown solid.

Provenance & Evidence