Hydrochloric Acid → HCID 70873624, compound

Participants

Reaction Steps

To a stirred solution of methyl 5-[ethyl(oxan-4-yl)amino]-4-methylpyridine-3-carboxylate (415 mg, 1.49 mmol) in THF (7 ml) and MeOH (3 ml) was added 4M NaOH solution (932 μl, 3.73 mmol). The reaction was stirred at room temperature for 4.5 h after which the solution was neutralised via the addition of 1M HCl and the solvent was removed under reduced pressure, followed by the addition of saturated brine (10 ml). The aqueous phase was extracted with 1:1 IPA:CHCl3 (3×50 ml), the combined organics washed with brine (30 ml), dried using Na2SO4, filtered and evaporated to afford the title compound as an off-white solid (305 mg, 77%) which was suitable for use in the next stage without any further purification. LC-MS 99%, m/z=265.1, 1H NMR (500 MHz, DMSO-d6) δ 8.57 (s, 1H), 8.46 (s, 1H), 3.82 (d, J=11.6 Hz, 2H), 3.25 (t, J=10.9 Hz, 2H), 3.16-2.99 (m, 3H), 2.45 (s, 3H), 1.64 (d, J=11.0 Hz, 2H), 1.48 (dt, J=11.9, 5.7 Hz, 2H), 0.81 (t, J=7.0 Hz, 3H).

Provenance & Evidence