Hydrochloric Acid → HCID 57898982, compound

Participants

Reaction Steps

Lithium aluminum hydride in ether (1.0 M, 3.86 ml, 3.86 mmol) was added to a solution of THF (50 mL) at 0° C., 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenoxy)acetic acid hydrochloride (Example 66; 0.380 g, 0.965 mmol) was added portionwise. The reaction was stirred for one hour, and then quenched with an excess of solid saturated sodium sulfate decahydrate. The reaction was stirred overnight and filtered, and the solid cake was washed several times with THF. The combined filtrates were concentrated and the residue was purified by MPLC (Biotage), eluting with ethyl acetate to afford the product as the free base. The free base was dissolved in ether, and 1M HCl in ether was added. The mixture was diluted with hexanes, filtered, and washed with hexanes to afford the title compound (0.065 g, 17.7% yield) as a white powder. 1H NMR (d6-DMSO) δ 2.22 (s, 3H), 3.66 (t, 2H), 3.95 (t, 2H), 6.60-6.76 (m, 5H), 6.85 (d, 1H), 7.35 (t, 1H), 8.19 (d, 1H).

Provenance & Evidence