2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine → HCID 86745701, compound

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To a solution of 2-[(3,7-dimethyl-2,6(E)-octadienyl)thio]-1H-1,3-benzimidazole from Example 1 (1.5 g, 5.2 mmol) and 3,5-dimethyl-4-methoxy-2-pyridylmethyl chloride (0.465 g, 5 2 mmol) in dimethylformamide (7 mL) at 0° C. under nitrogen was added dropwise triton-B (5 mL of a 40% solution). The solution was stirred at ambient temperature for 72 hours, then at 50° C. for 48 hours. Evaporation of the solvent gave a residue which was dissolved in CH2Cl2, washed with water and dried over Na2SO4. Evaporation of the solvent and flash chromatography of the resultant oil (10% Et2O/CH2Cl2, Merck Kieselgel) gave 1.1 g of 1-(3,5-dimethyl-4-methoxy-2-pyridylmethyl)-2-[(3,7-dimethyl-2,6(E)-octadienyl)thio]-1H-1,3-benzimidazole (free base) which was converted to its oxalate salt (1.36 g). m.p. 76°-80° C. NMR (DMSO-d6) δ7.93(s,1H), 7.5(m,1H), 7.1(m,3H), 5.4(s,2H), 5.37(m,1H), 5.07(m,1H), 3.93(m,2H), 3.70(s,3H), 2,27(s,3H), 2.15(s,3H), 2.0(m,4H), 1.6(s,3H), 1.53(s,3H), 1.07(s,3H).

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