Potassium hydroxy sulfite → 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester

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Reaction Steps

To a mixture of 3,4-diamino-N-quinolin-2-yl-benzamide (1.0 g, 3.92 mmol) and 3-(4-formyl-3,5-dimethyl-phenyl)-propionic acid methyl ester (1.09 g, 3.92 mmol) in DMF (10 mL) and water (1 mL) was added oxone (1.62 g, 2.63 mmol) and the mixture was stirred atambient temperature for 20 min. The mixture was quenched with water and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (1:3) to give 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester as a pale yellow solid. 1H NMR (Methanol-d4, 400 MHz): δ 8.45 (d, 1H), 8.38 (d, 1H), 8.29 (s, 1H), 8.04 (d, 1H), 7.93 (d, 2H), 7.83 (s, 1H), 7.75 (m, 1H), 7.55 (m, 1H), 7.09 (s, 2H), 3.67 (s, 3H), 2.97 (t, 2H), 2.71 (t, 2H), 2.16 (s, 6H). MS (m/z) 479.2 (M+1); Retention time: 1.48 min (Method 10).

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