Methylamine → HCID 76285219, compound

Participants

Reaction Steps

To a solution of 2-(ethylthio)-4-methyl-1,7-naphthyridine-3-carboxylic acid (0.25 g, 1.01 mmol, 1 eq) in dry THF (12 ml) were added HATU (0.42 g, 1.11 mmol, 1.1 eq) and TEA (0.4 ml, 3.03 mmol, 3 eq) at RT and the reaction mixture was stirred at RT for 15 min. 3-fluorophenyl)methanamine (0.16 g, 1.26 mmol, 1.25 eq) was added to the mixture at RT and the reaction mixture was stirred at RT for 1 h. Afterwards the excess solvent was distilled off and the residue was diluted with a sat. aq. solution of NH4Cl (50 ml). The aq. part was extracted with EtOAc (3×80 ml). The combined organic layers were washed with a sat. aq. solution of NaHCO3 (50 ml), water (50 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which was purified by CC (acetone/hexane 2:9) to yield 2-Ethylsulfanyl-N-[(3-fluorophenyl)-methyl]-4-methyl-[1,7]naphthyridine-3-carboxylic acid amide (example 2) (0.18 g, 0.51 mmol, 50%). MS m/z [M+H]+ 356.1.

Provenance & Evidence