Diisopropylethylamine → HCID 70873876, compound

Participants

Reaction Steps

To a solution of 5-chloro-2-methoxy-3-[methyl(oxan-4-yl)amino]benzoic acid (200 mg, 0.67 mmol) in DMF (2 ml) at room temperature under nitrogen was added HBTU (304 mg, 0.80 mmol) followed by N-ethyl-N-(propan-2-yl)propan-2-amine (174 μl, 1.0 mmol) and 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 125 mg, 0.73 mmol). After stirring for 2 hours at room temperature EtOAc (30 ml) was added to the reaction mixture and this was then washed with deionized water (5 ml) followed by saturated NaHCO3(aq) (3×5 ml). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by FCC (10 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 96:4 DCM:MeOH) to give 182 mg (63%) of the title compound as an off-white solid. LC-MS 98%, m/z=434.1/436.1, 1H NMR (500 MHz, Chloroform-d) δ ppm 12.52 (br s, 1H), 8.76 (t, J=5.8 Hz, 1H), 7.69 (d, J=2.6 Hz, 1H), 7.01 (d, J=2.6 Hz, 1H), 5.94 (s, 1H), 4.56 (d, J=6.0 Hz, 2H), 3.99 (dd, J=11.2, 3.9 Hz, 2H), 3.72 (s, 3H), 3.49 (tt, J=11.5, 3.7 Hz, 1H), 3.36 (t, J=11.2 Hz, 2H), 2.67 (s, 3H), 2.42 (s, 3H), 2.31 (s, 3H), 1.93-1.73 (m, 2H), 1.64-1.52 (m, 2H).

Provenance & Evidence