Hydrochloric Acid → 6-[2-(2-Chloro-phenyl)-5-(4-propoxy-phenyl)-pyrrol-1-ylmethyl]-pyridin-2-ylamine hydrochloride

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Reaction Steps

A solution of 6-[2-(2-chloro-phenyl)-5-(4-propoxy-phenyl)-pyrrol-1-ylmethyl]-pyridin-2-ylamine (50.0 mg, 0.12 mmol) and HCl (0.06 mL of a 2.0 M solution in diethyl ether, 0.12 mmol) in diethyl ether (10 mL) was stirred at room temperature for 30 min. The mixture was concentrated and the solid obtained triturated with hexanes to afford the title compound (48.0 mg g, 88%) as an off-white solid: Rf 0.65 (50:50 hexanes/ethyl acetate); mp 68-76° C.; 1H NMR (300 MHz, CDCl3) δ 7.20-7.60 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 6.65 (br s, 1H), 6.45 (d, J=8.2 Hz, 1H), 6.39 (d, J=3.6 Hz, 1H), 6.35 (d, J=3.6 Hz, 1H), 5.75 (d, J=8.2 Hz, 1H), 5.24 (s, 2H), 3.93 (t, J=6.6 Hz, 2H), 1.80 (tq, J=7.5, 6.6 Hz, 2H), 1.04 (t, J=7.5 Hz, 3H); IR (ATR) 3292, 3105, 2964, 2711, 1661, 1628, 1486, 1244, 1174, 833, 755, 722 cm−1; ESI MS m/z 418 [C25H24ClN3O+H]+; HPLC (Method 1) 97.1% (AUC), tR=14.53 min. Anal. Calcd for C25H24ClN3O.HCl.0.5H2O: C, 64.80; H, 5.66; N, 9.07. Found: C, 64.63; H, 5.50; N, 8.65.

Provenance & Evidence