Hydrochloric Acid → HCID 70874152, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-chloro-2-ethyl-3-[methyl(oxan-4-yl)amino]benzoate (334 mg, 1.07 mmol) in THF (11 ml) was added 4M NaOH (10.7 ml). The reaction mixture was stirred at 50° C. for 27 hours. MeOH (5 ml) was added to the reaction mixture and this was stirred for a further 21 hours at 50° C. The reaction mixture was acidified to pH 2-3 with 6M HCl and extracted with DCM (5×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give 311 mg of the title compound as an orange oil that solidified upon standing. The material was taken through the next step without further purification. LC-MS 79%, 2.01 min (3 minute LC-MS method), m/z=298.0/300.0, 1H NMR (500 MHz, Chloroform-d) δ ppm 7.72 (d, J=2.1 Hz, 1H), 7.37-7.27 (m, 1H), 4.00 (brd, J=11.1 Hz, 2H), 3.36 (td, J=11.6, 2.0 Hz, 2H), 3.11 (q, J=7.4 Hz, 2H), 2.94 (t, J=10.6 Hz, 1H), 2.64 (s, 3H), 1.78-1.56 (m, 4H), 1.15 (t, J=7.4 Hz, 3H).

Provenance & Evidence