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Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5 h; Stage #2: at 20℃; for 4 h;
[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).
N-[4-(pyridine-4-yloxy)phenyl]-1H-benzimidazole-2-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
99%
0.064 mmol of benzimidazolecarboxylic acid 41 was dissolved in DMF together with 0.064 mmol of the amine 5a, a solution of TBTU (0.096 MMOL) in DMF, HOBT (0. 026 MMOL) in DMF and 0.32 mmol of DIPEA were added successively, and the mixture was stirred overnight at room temperature. A further 0. 25 eq. of acid was added, and the mixture was stirred for 4 hours. The reaction mixture was diluted with water and extracted a number of times with ethyl acetate. The combined organic phases were washed 2 x with water, dried, filtered and evaporated. Yield : 99%, colourless solid
[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 (60% 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 50% 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 20-100% ethyl acetate in hexanes to give the title compound as a white powder (109 mg, 39%).
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