Hydrochloric Acid → 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)-benzimidazole-5-carboxylic acid

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To a suspension of methyl 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)—benzimidazole-5-carboxylate (82 mg, 0.23 mmol) in CH3CN (2.5 mL) and methanol (2 mL) was added 1N LiOH (2.3 mL, 10 eq.). The reaction mixture was stirred at room temperature for 3 days, acidified with 1N HCl (2.4 mL), filtered and dried to yield 1-[(7-cyano-2-naphthyl)methyl]-2-oxo-(3H)—benzimidazole-5-carboxylic acid (72 mg, 91%) as a white solid. 1H NMR(CDCl3) δ: 5.16 (s, 2H); 6.77-6.79 (d, 1H); 7.50-7.54 (t, 2H); 7.62-7.64 (dd, 1H); 7.68 (s, 1H); 7.72 (s, 1H); 7.78-7.84 (dd, 2H); 8.11 (s, 1H); 10.8 (s, 1H). ES-MS (M+H)+=344.1.

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