5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide → HCID 22346299, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-[1,6]naphthyridine-7-carboxamide (0.57 g, 1.5 mmol), N,N-dimethyl-2-[(methylsulfonyl)amino]acetamide from Step 1 (0.25 g, 1.38 mmol) and copper (I) oxide (0.10 g, 0.70 mmol) in pyridine (5 mL) was heated in an oil bath at 115° C. overnight. The resultant mixture was concentrated under vacuum. To the residue, chloroform (200 mL) and a saturated aqueous solution of ethylenediamine tetraacetic acid, disodium salt (75 mL) was added. The mixture was stirred vigorously at room temp for 2 hours in the presence of air, and filtered through a pad of Celite. The organic extract was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was dissolved in DMSO and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as white solid.

Provenance & Evidence