Hydroxylamine → 2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-5-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine

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Reaction Steps

[step 3] 5-Cyanomethyl-2-(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[b,f]azepine (200 mg, 0.47 mmol) obtained in step 2 was dissolved in ethanol (4 mL), and the solution was added with hydroxylamine (50% aqueous solution, 0.15 mL, 2.37 mmol), followed by heating under reflux for 1 hr. The mixture was concentrated under reduced pressure. The obtained residue was dissolved in DMF (1 mL) and the solution was added with pyridine (46 μL, 0.57 mmol) and ethyl chlorocarbonate (54 μL, 0.57 mmol) at 0° C., followed by stirring at room temperature for 2 hr. Ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added thereto. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in toluene (10 mL), and the solution was added with potassium tert-butoxide (51 mg, 0.45 mmol), followed by stirring at room temperature for 15 min. Ethyl acetate was added to the mixture, and the organic layer was washed with 5% aqueous citric acid solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (compound 1, 190 mg, 83%).

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