Potassium Carbonate → HCID 178443482, compound

Participants

Reaction Steps

To a solution of 4-(cyclohexylamino)-1-(4-iodophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one dihydrochloride (400 mg, 0.76 mmol, intermediate II.1.c.1) in DMF (6 mL) was added diisopropylethylamine (0.333 mL, 1.9 mmol) and the reaction mixture was stirred at rt for 10 min. Potassium carbonate (210 mg, 1.52 mmol) and 9-iodononene (230 mg, 0.91 mmol, prepared from 9-hydroxynonene, iodine, triphenylphosphine and imidazole) were added. The reaction mixture was stirred at 100° C., sealed, for 1 h. The reaction mixture was diluted with ethyl acetate, washed with water. The organic layer was concentrated in vacuo and the residue was purified by reverse phase preparative HPLC (5- 95% MeCN/H2O containing 0.1% TFA, C18). The desired fractions were basified with aqueous NaHCO3, extracted with EtOAc, washed with brine, dried over sodium sulfate and concentrated in vacuo to provide the desired compound as a light brown solid. LRMS (M+1)=577.

Provenance & Evidence