Diisopropylethylamine → HCID 70873846, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-chloro-3-[ethyl(oxan-4-yl)amino]benzoic acid (109 mg, 0.3 mmol) in DMF (3 ml) at room temperature under nitrogen was added PyBOP (187 mg, 0.36 mmol) followed by N-ethyl-N-(propan-2-yl)propan-2-amine (78 μl, 0.45 mmol) and 3-(aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-one (89%, 56 mg, 0.33 mmol). After stirring for 1 hour at room EtOAc (30 ml) was added to the reaction mixture and this was then washed with deionized water (2×10 ml) followed by saturated NaHCO3(aq) (2×10 ml). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified twice by FCC (5 g silica, Isolute cartridge, gradient of eluents; 100% DCM to 98:2 DCM:MeOH). The sample was dried in a vacuum oven for 18 hours to give 103 mg (65%) of the title compound as a pale yellow solid. LC-MS 94%, m/z=496.0/498.0/500.0, 1H NMR (500 MHz, Chloroform-d) δ 11.00 (s, 1H), 7.20-7.10 (m, 1H), 7.10-7.05 (m, 2H), 5.94 (s, 1H), 4.54 (d, J=5.9 Hz, 2H), 3.96 (d, J=11.4 Hz, 2H), 3.42-3.26 (m, 2H), 3.28-3.12 (m, 1H), 3.09 (q, J=7.0 Hz, 2H), 2.39 (s, 3H), 2.23 (s, 3H), 1.72 (td, J=8.5, 3.8 Hz, 4H), 0.90 (t, J=7.0 Hz, 3H).

Provenance & Evidence