Reaction Steps
A solution containing amine 50 (197 mg, 0.41 mmol) in DCM (10 mL) was cooled to 0° C. TEA (73 mg, 0.72 mmol) was added followed by cyclopropanecarbonyl chloride (57 mg, 0.55 mmol) and the reaction mixture was warmed to ambient temperature. After 16 h, the reaction mixture was diluted with DCM and the resulting organic solution was washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 247 mg of 57 as a yellow-colored oil which was used without further purification. 1H NMR (300 MHz, CDCl3), mixture of amide rotamers: δ8.70 (s, 0.5H), 8.60 (s, 0.5H), 8.25 (dd, J=5.4, 8.7 Hz, 0.5H), 8.10 (dd, J=5.1, 8.7 Hz, 0.5H), 7.03-6.99 (m, 1H), 6.97-6.89 (m, 1H), 6.80 (s, 1H), 5.38 (app t, J=9.3 Hz, 1H), 4.81 (d, J=5.1 Hz, 1H), 4.57-4.50 (m, 2H), 4.37 (app t, J=7.8 Hz, 1H), 4.24 (d, J=10.5 Hz, 1H), 4.16-4.04 (m, 2H), 3.93 (d, J=5.4 Hz, 1H), 3.81-3.73 (m, 1H), 3.54-3.40 (m, 2H), 2.41-2.37 (m, 1H), 1.79-1.60 (m, 8H), 1.45 (s, 9H), 1.21-1.09 (m, 6H), 1.04-1.01 (m, 3H), 0.91-0.86 (m, 1H) ppm. Mass spectrum, m/z [553.4] (M+H)+.
