Hydroxylamine → HCID 178437422, compound

Participants

Reaction Steps

(E)-[2-(2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetonitrile (JP-B-2526005; 220 mg, 0.53 mmol) was dissolved in ethanol (5 mL), hydroxylamine (50% aqueous solution, 0.48 mL, 7.63 mmol) was added, and the mixture was heated under reflux for 16 hr, and concentrated under reduced pressure. The obtained residue was dissolved in acetonitrile (5 mL), N,N′-thiocarbonyldiimidazole (141 mg, 0.79 mmol) and DBU (315 μL, 2.11 mmol) were added, and the mixture was stirred at room temperature for 2 hr. 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. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give the title compound (compound 8) (67 mg, 26%).

Provenance & Evidence