Sodium Hydroxide → 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazole

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Reaction Steps

The title compound (0.45 g, 50%) was prepared by the general procedure using 6-fluoro-5-(piperidin-1-yl)-2-mercapto-1H-benzimidazole (0.5 g, 2.0 mmol) (obtained in preparation 3), 3-methyl-4-(2,2,2,-trifluoroethoxy)-2-chloromethylpyridine hydrochloride (0.47 g, 2.0 mmol), sodium hydroxide (0.16 g, 4.0 mmol) and ethanol (10 mL). mp 160-161° C.; 1R (KBr) 3122, 1585, 1432 cm-1 ; 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.80 (m, 4H, (CH2)2), 2.38 (s, 3H, CH3), 3.00 (m, 4H, N(CH2)2), 4.40 (s, 2H, SCH2), 4.46 (q, J=7.8 Hz, 2H, OCH2CF3), 6.74 (d, J=5.5 Hz, 1H), 7.18 (d, J=7.6 Hz, 1H), 7.26 (d, J=10.0 Hz, 1H), 8.42 (d, J=5.5 Hz, 1H), 12.50 (s, 1H, NH); Mass (m/z) 454 (M+).

Provenance & Evidence