Triethylamine → N-[[3-fluoro-4-(2-hydroxyethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide

Participants

Reaction Steps

45 μl oxalyl chloride (0.53 mmol) was added to a mixture of 50 mg 2-methyl-1,8-naphthyridine-3-carboxylic acid (0.27 mmol) in 3 ml CH2Cl2 with one drop DMF. The reaction mixture was stirred for 1.5 h and then evaporated to dryness under reduced pressure. The residue was dissolved in 3 ml CH2Cl2. 4 mg DMAP (0.03 mmol) and 188 μl triethyl amine (1.35 mmol) were added to the solution followed by 54 mg 2-[[4-(aminomethyl)-2-fluoro-phenyl]methoxy]ethanol (0.27 mmol). The reaction mixture was stirred for 4 h and then diluted with water. The phases were separated and the aqueous phase was extracted with CH2Cl2. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (SiO2, CH2Cl2/MeOH 20:1) gave 36 mg (36%) of the title compound.

Provenance & Evidence