Triethylamine → 1-(3-Acetyl-4-methoxyphenyl)-3-(2-methyl-[1,5]-naphthyridin-4-yl)urea

Participants

Reaction Steps

3-Acetyl-4-methoxybenzoic acid (0.082 g) in toluene (4 ml) was treated with triethylamine (0.176 ml) and subsequently with diphenylphosphoryl azide (0.092 ml). The mixture was stirred for 16 h at room temperature, D2 (0.067 g) added and the mixture heated to reflux for 4 h. After cooling to room temperature solvent was removed at reduced pressure and the residue column chromatographed (silica gel, 0-10% methanol in DCM containing 1% ammonia) to give the title compound (0.03 g) as a colourless solid. H NMR δ: 2.55 (3H, s), 2.63 (3H, s), 3.89 (3H, s), 7.18 (1H, d), 7.68 (1H, dd), 7.77-7.83 (2H, m), 8.28 (1H, dd), 8.34 (1H, s), 8.89 (1H, m), 9.85 (1H, s), 10.03 (1H, s). m/z (API+): 351 (MH+).

Provenance & Evidence