Potassium Carbonate → HCID 69431031, compound

Participants

Reaction Steps

Under nitrogen, the cis-3-[(4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)oxy]cyclohexanamine (90 mg, 0.273 mmol) obtained in Example 724 was dissolved in N,N-dimethylacetamide (2 ml), followed by adding thereto bis(2-bromoethyl) ether (34 μl, 0.273 mmol) and potassium carbonate (94 mg, 0.683 mmol), and the resulting mixture was stirred at 80° C. for 6 hours. The reaction solution was cooled to room temperature and a 1N-aqueous sodium hydroxide solution was added thereto, followed by extraction with chloroform (three times). The combined chloroform layer was washed with a saturated aqueous sodium chloride solution, dried by the addition of anhydrous magnesium sulfate, and then filtered. The solvent was distilled off under reduced pressure and the resulting concentration residue was purified by a silica gel column chromatography (eluent: acetonitrile/aqueous ammonia=100/0, 100/1) to obtain 4-methyl-5-[(cis-3-morpholin-4-ylcyclohexyl)oxy]-1-tetrahydro-2H-pyran-2-yl-1H-indazole (83 mg, yield 76.0%) as light-yellow tar.

Provenance & Evidence