1H-Benzimidazole-2-carboxylicacid,1-methyl-,methylester(9CI)

To a solution of lH-benzoimidazole-2-carboxylic acid methyl ester (18) (177 mg, 1.0 mmol) in dry DMF (5 mL) was added sodium hydride (applied as 60percent> dispersion in oil, 62 mg, 1.5 mmol)) at 0°C under NIn the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 1-methylbenzimidazole (60.0 μl, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 ° C for 24 hours under normal pressure. Cooled to 65 ° C, methyl iodide (93 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 50percent.[00188] To a suspension of 1H-benzo[d]imidazole-2-carboxylic acid (240 mg, 1.5 mmol) in DMF (7 ml) was added sodium hydride (60percent dispersion in mineral oil) (130 mg, 3.7 mmol). The reaction stuffed at room temperature for 30 mm. Methyl iodide (0.46 ml, 7.3 mmol) was added. After 4 h at room temperature, the reaction was quenched with saturated ammonium chloride. The aqueous layer was extracted with 50percent ethyl acetate in hexanes. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by column chromatography eluting with 20-100percent ethyl acetate in hexanes to give the title compound as a white powder (109 mg, 39percent).To a solution of lH-benzoimidazole-2-carboxylic acid methyl ester (18) (177 mg, 1.0 mmol) in dry DMF (5 mL) was added sodium hydride (applied as 60percent> dispersion in oil, 62 mg, 1.5 mmol)) at 0°C under NIn the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 1-methylbenzimidazole (60.0 μl, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 ° C for 24 hours under normal pressure. Cooled to 65 ° C, methyl iodide (93 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 50percent.[00188] To a suspension of 1H-benzo[d]imidazole-2-carboxylic acid (240 mg, 1.5 mmol) in DMF (7 ml) was added sodium hydride (60percent dispersion in mineral oil) (130 mg, 3.7 mmol). The reaction stuffed at room temperature for 30 mm. Methyl iodide (0.46 ml, 7.3 mmol) was added. After 4 h at room temperature, the reaction was quenched with saturated ammonium chloride. The aqueous layer was extracted with 50percent ethyl acetate in hexanes. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by column chromatography eluting with 20-100percent ethyl acetate in hexanes to give the title compound as a white powder (109 mg, 39percent).

Molecular Weight:190.20
XLogP3:1.5
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:190.074227566
Monoisotopic Mass:190.074227566
Topological Polar Surface Area:44.1
Heavy Atom Count:14
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes