Sodium Azide → HCID 58674469, compound

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A solution of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-[(2-cyanopyridin-4-yl)oxy]phenyl}propanamide (0.300 g, 0.67 mmol), aluminum trichloride (1.0 M in hexanes, 2.0 mL, 2.0 mmol), and sodium azide (0.131 g, 2.0 mmol) in DMF was heated at 100° C. for 3 days. The mixture was concentrated and purified by column chromatography to give A-57 which was converted to the bishydrochloride salt (29 mg). 1H NMR (400 MHz, CD3OD; bis HCl salt) δ: 8.66 (d, 1H), 8.03 (d, 1H), 7.93 (d, 1H), 7.66 (dd, 1H), 7.52 (t, 1H), 7.45 (d, 1H), 7.41 (dd, 1H), 7.37 (d, 1H), 7.21-7.24 (m, 1H), 7.12-7.17 (m, 1H), 3.10 (t, 2H), and 2.75 (t, 2H). LCMS, FA: Rt=1.48 min, [MH+ 489.3].

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