Pyridine → 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-pheny-1H-indene-2-carboxylic acid cyclohexylamide

Participants

Reaction Steps

6-(2-Morpholine-4-ylethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (130 mg, 0.28%) obtained in Step 4 was dissolved in ethanol (20 mL), and hydroxylamine hydrochloride (60 mg, 0.85 mmol) and pyridine (892 mg, 1.13 mmol) were added thereto. The mixture was refluxed for 1 hr, and cooled to RT, and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 86 mg of 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (yield: 64%). Subsequently, 1-hydroxyimino-6-(2-morpholine-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexylamide (80 mg, 0.17 mmol) thus obtained was dissolved in methanol (20 mL) and 10%-palladium (100 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. Then, the resulting residue was purified by flash chromatography to obtain 14 mg of the titled compound (yield: 18%).

Provenance & Evidence