Tetrahydrofuran → HCID 66818620, compound

Participants

Reaction Steps

A mixture of 8-[2-(4-amino-3-iodo-2,6-dimethyl-phenyl)-ethanesulfonyl]-2-(4-methyl-cyclohexyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (15 mg, 0.0256 mmol), palladium acetate (1.1 mg, 5.11 μmol), 1,1′-bis(diphenylphosphino)ferrocene (2.2 mg, 5.11 μmol), tert-butyl isocyanate (12 μL, 0.0767 mmol) and N,N-diisopropylethylamine (13 μL, 0.0767 mmol) in tetrahydrofuran (1 mL) was heated with stirring for 12 hours in a pressure bottle sealed under the conditions of 4 atm and 80° C. in a carbon monoxide atmosphere. After returning to room temperature, palladium acetate (2.2 mg, 10.22 μmol), 1,1′-bis(diphenylphosphino)ferrocene (4.4 mg, 10.22 μmol), tert-butyl isocyanate (24 μL, 0.153 mmol) and N,N-diisopropylethylamine (26 μL, 0.153 mmol) were added to the reaction solution, and the mixture was heated with stirring for 14 hours in a pressure bottle sealed under the conditions of 4 atm and 80° C. in a carbon monoxide atmosphere. After returning to room temperature, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by preparative TLC to give 3-tert-butyl-5,7-dimethyl-6-{2-[2-(4-methyl-cyclohexyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-1H-quinazoline-2,4-dione as a pale yellow solid (3.3 mg, 22%).

Provenance & Evidence