1,2-Dichloroethane → 4-(5-bromo-2-chloropyrimidin-4-yl)-N-((S)-1-(p-tolyl)ethyl)morpholine-3-carboxamide

Participants

Reaction Steps

The title compound was prepared in a manner similar to PREPARATION x31 using 4-(5-bromo-2-chloropyrimidin-4-yl)morpholine-3-carboxylic acid (PREPARATION x30, 1 g, 3.10 mmol), EDC (0.892 g, 4.65 mmol), HOBt (0.712 g, 4.65 mmol), triethylamine (1.296 mL, 9.30 mmol) and (S)-1-p-tolylethanamine (0.629 g, 4.65 mmol) in DMF (15 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.37 (dd, J=6.95, 3.66 Hz, 3 H), 2.27 (s, 3 H), 3.55 (d, J=9.35 Hz, 2 H), 3.66-3.77 (m, 1 H), 3.82-3.92 (m, 1 H), 4.21-4.39 (m, 2 H), 4.83-5.01 (m, 2 H), 7.12 (d, J=7.83 Hz, 2 H), 7.16-7.28 (m, 2 H), 8.45 (d, J=10.86 Hz, 2 H). ESI-MS m/z [M+H]+ calc'd for C18H20BrClN4O2, 439.05; found 439.2.

Provenance & Evidence