Hydrochloric Acid → HCID 178523279, compound

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Reaction Steps

2-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-1H-benzoimidazole-5-carboxylic acid (0.05g, 0.111 mmol) was dissolved in anhydrous dimethylformamide (0.5 mL) and the solution was combined with 1-hydroxybenzotriazole hydrate (0.017 g, 0.126 mmol), benzotriazole-1-yloxytrispyrrolidinophosphoniurnhexafluoro-phosphate (0.063 g, 0.121 mmol) and N-methylmorpholine (0.013 mL, 0.118 mmol) at room temperature under an atomosphere of dry N2. After 2 minutes 4-phenylbutylamine (0.02 mL, 0.127 mmol) was added and the mixture was stirred at room temperature for 2 hours. The mixture was transferred to a sparatory funnel containing 20% ethanol/ethyl acetate solution (7 mL), 0.2N HCl (3.5 mL) and saturated aqueous NaCl (3.5 mL). The aqueous phase was extracted once with 20% ethanol/ethyl acetate solution (7 mL) and the combined organic phases were washed with a solution containing 0.2N HCl (3.5 mL) in saturated aqueous NaCl (3.5 mL) followed by a final washing with saturated aqueous sodium bicarbonate solution (7 mL). The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated to dryness on a rotary evaporator to provide 2-[5-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H-benzoimidazol-2-ylmethyl]-N-(3-phenylpropyl)-1H-benzoimidazole-5-carboxamide as crude material (0.14 g).

Provenance & Evidence