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

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Reaction Steps

The title compound (1.48 g, 64%) was prepared by the general procedure using 6-fluoro-5-(4-methylpiperazin-1-yl)-2-mercapto-1H-benzimidazole (1.33 g, 5.0 mmol) (obtained in preparation 4), 3-methyl-4-(2,2,2-trifluoroethoxy)-2-chloromethylpyridine hydrochloride (1.5 g, 5.5 mmol), sodium hydroxide (0.4 g, 10.0 mmol) and ethanol (25 mL). mp 109-110° C.; IR (KBr) 3397, 1584, 1258 cm-1 ; 1H NMR (DMSO-d6) δ 2.38 (s, 3H, CH3), 2.80 (s, 3H, CH3), 3.12 (m, 4H, N(CH2)2), 3.40 (m, 4H, N(CH2)2), 4.48 (q, J=7.9 Hz, 2H, OCH2CF3), 4.60 (s, 2H, SCH2), 6.80 (d, J=5.8 Hz, 1H), 7.14 (d, J=7.1 Hz, 1H), 7.24 (d, J=11.7 Hz, 1H), 8.40 (d, J=5.5 Hz, 1H); Mass (m/z) 469 (M+).

Provenance & Evidence