Methylamine → 4-(4-Cyano-2-methylsulfanyl-phenyl)-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,4,5,6,7,8-hexahydro-2H-quinazoline-3-carboxylic acid methylamide

Participants

Reaction Steps

To a mixture of 4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydroquinazoline-4-yl]-3-methylsulfanyl-benzonitrile (INTERMEDIATE 6; 82 mg; 0.179 mmol) and diisopropylethylamine (100 μL; 0.588 mmol) in acetonitrile (1 mL) is added 4-nitrophenylchloroformate (170 mg; 0.843 mmol) and 4-dimethylaminopyridine (210 mg; 1.719 mmol) in little portions over 19 h at room temperature. Methylamine (1M in THF; 1 mL; 1.00 mmol) is added to the mixture containing the 4-nitro-phenyl carbamate intermediate and the mixture is stirred at room temperature for 30 min. The reaction mixture is purified by reversed phase HPLC (Sunfire, gradient of acetonitrile in water, 0.1% TFA). Yield: 63 mg. ESI mass spectrum: [M+H]+=515; Retention time HPLC: 1.11 min (Z018_S04).

Provenance & Evidence