Reaction Steps
(see, e.g., WO2013039988A1). A pressure vessel was charged with 50 (121 mg, 0.29 mmol), 4-(2-aminoethyl)morpholine (1.0 mL, 7.6 mmol) and iPrOH (3 mL) and NMP (1 mL). The vessel was sealed and the reaction mixture was heated at 150° C. overnight. The reaction mixture was diluted with EtOAc (20 mL) and washed with H2O (10 mL×3) to remove NMP. Combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. Crude was subjected to flash column chromatography on silica gel to provide the title compound (40 mg, 26%) as a yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.29 (q, J=7.1, 6.6 Hz, 4H), 7.07 (t, J=7.1 Hz, 1H), 6.96 (d, J=8.6 Hz, 2H), 6.91 (d, J=8.3 Hz, 2H), 6.78 (s, 1H), 5.46 (s, 2H), 4.43 (q, J=7.1 Hz, 2H), 3.76-3.70 (m, 4H), 3.55 (q, J=5.0 Hz, 2H), 2.63 (t, J=5.7 Hz, 2H), 2.58 (s, 3H), 2.49 (s, 4H), 1.42 (t, J=7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 166.00, 157.47, 157.15, 156.51, 152.39, 141.23, 134.44, 132.67, 129.66, 129.31, 123.18, 118.83, 118.77, 107.03, 103.90, 66.92, 61.62, 57.03, 53.40, 49.37, 37.75, 16.16, 14.26.
