Diisopropylethylamine → HCID 68508908, compound

Participants

Reaction Steps

A mixture of 4-[4-allyloxycarbonyl-2-(2-bromo-acetylamino)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (23.0 g, 46.33 mmol, 1.0 equiv) and N-ethyldiisopropylamine (11.98 g, 92.67 mmol,2.0 equiv) in toluene (250 mL) was heated to reflux. After 8 h, the reaction mixture was cooled, washed with water and concentrated by evaporation under reduced pressure and purified with silica column chromatography eluting with dichloromethane/acetone (95:5) to obtain 10.0 g (52%) of the title compound as yellow solid. 1H NMR (400 MHz, DMSO): δ 1.41 (s, 9H), 1.65 (br s, 4H), 2.89 (s, 2H), 3.74 (s, 2H), 3.90 (br s, 1H), 4.05 (br s, 2H), 4.73 (d, J=5.1, 2H), 5.25 (d, J=10.4, 1H), 5.36 (dd, J=17.2 Hz, J=1.1 Hz, 1H), 5.98-6.05 (m, 1H), 6.95 (d, J=8.7 Hz, 1H), 7.44 (d, J=1.4 Hz, 1H), 7.53 (dd, J=17.2 Hz, J=1.1 Hz, 1H), 10.58 (s, 1H). 13C-NMR (100 MHz, DMSO): δ 26.87, 28.02, 45.15, 53.36, 64.35, 78.67, 110.81, 115.77, 117.36, 118.04, 125.21, 126.61, 132.95, 132.99, 138.63, 153.70, 164.94, 165.00. MS (ISP): 416.2 [M+H]+.

Provenance & Evidence