N-Methyl dicyclohexylamine → HCID 90224890, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-(trifluoromethyl)phenyl)-8-(vinylsulfonyl)-1,3,8-triazaspiro[4.5]deca-1-en-4-one (150 mg, 0.387 mmol) synthesized according to the method described in Schemes 2, 3, and 12 of WO2010/126030(A1), 1-(4-bromo-3,5-dimethylphenyl)-5,5-dimethylimidazolidine-2,4-dione (169 mg, 0.542 mmol), bis(dibenzylidineacetone) palladium (45 mg, 0.077 mmol), tri-tert-butylphosphine tetrafluoroboric acid (22 mg, 0.077 mmol), and methyldicyclohexylamine (0.123 mL, 0.581 mmol) in N-methyl-2-pyrrolidone (0.97 mL) was stirred at 100° C. for one hour under nitrogen atmosphere. The reaction mixture was cooled, quenched with water, and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate-hexane) to afford (E)-1-(3,5-dimethyl-4-(2-((4-oxo-2-(3-(trifluoromethyl)phenyl)-1,3,8-triazaspiro[4.5]deca-1-en-8-yl)sulfonyl)vinyl)phenyl)-5,5-dimethylimidazolidine-2,4-dione (197 mg, 82%).

Provenance & Evidence