1,1'-Carbonyldiimidazole → 2-Methoxy-5-[3-(2-methyl-[1,5]-naphthyridin-4-yl)ureido]benzoic Acid Methyl Ester

Participants

Reaction Conditions

Reaction Steps

D2 (0.51 g) was added in portions over 10 min to a solution of 1,1′-carbonyl diimidazole (0.536 g) and 4-N,N-dimethylaminopyridine (0.004 g) in DMF (10 ml). The resulting solution was stirred for 16 h, 5-amino-2-methoxybenzoic acid methyl ester (0.577 g) added in DMF (2 ml) and the mixture heated at 100° C. for 2 h. The mixture was diluted with ethyl acetate and washed with water (×2) and brine, dried (Na2SO4) and solvent removed at reduced pressure. The pale pink solid was triturated with DCM to give the title compound (0.58 g). 1H NMR δ: 2.64 (3H, s), 3.34 (3H, s), 3.81 (3H, s), 7.15 (1H, d), 7.59 (1H, dd), 7.80 (1H, dd), 7.94 (1H, d), 8.29 (1H, dd), 8.34 (1H, s), 8.89 (1H, m), 9.85 (1H, s), 10.05 (1H, s).

Provenance & Evidence