Sodium Hydroxide → HCID 178502871, compound

Participants

Reaction Steps

To a mixture of quinoline-6-carbothioic acid 4-benzyloxy-benzylamide described in Preparation Example E+-10 (57 mg, 0.15 mmol) and acetonitrile (3 mL) was added 2-(bromomethyl)naphthalene (200 mg, 0.94 mmol), which was then refluxed for 2 hours. After cooling, the solvent was evaporated in vacuo, and the residue was washed with diethyl ether three times. A mixture of a portion (29 mg) of the resulting crude product (57 mg), methoxylamine hydrochloride (2.9 mg, 0.035 mmol), an aqueous solution of 1N sodium hydroxide (0.035 mL, 0.035 mmol) and N-methylpyrrolidinone (1 mL) was stirred at room temperature for 25 minutes. The reaction solution was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and ditrifluoroacetic acid salt of the title compound (1.9 mg, 0.0030 mmol, 6.4%) was obtained.

Provenance & Evidence