Ethyl Acetate → {2-[3-(4-Bromo-2-dimethylcarbamoyl-phenyl)-ureido]-ethyl}-methyl-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (2-amino-ethyl)-methyl-carbamic acid tert-butyl ester (100 mg, 0.574 mmol) in DMF (2 mL) was added diisopropylethylamine (0.3 mL, 1.75 mmol) and 5-bromo-2-isocyanato-N,N-dimethyl-benzamide (154 mg, 0.572 mmol). The solution was stirred for 18 hours at 80° C. Ethyl acetate was added to the reaction mixture, and the combined mixture was washed 3 times with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was recrystallized from a mixture of ethyl acetate and dichloromethane to give 75 mg (30%) of {2-[3-(4-bromo-2-dimethylcarbamoyl-phenyl)-ureido]-ethyl}-methyl-carbamic acid tert-butyl ester. 1H-NMR (250 MHz, CDCl3) δ 11.0 (br s, 1H), 8.35 (d, J=9.1 mmol), 7.77 (s, 1H), 7.57 (s, 1H), 7.42 (d, J=9.0 Hz, 1H), 3.45-3.55 (m, 5H), 2.97 (s, 6H), 2.86 (s, 3H), 1.12 (s, 9H).

Provenance & Evidence