Morpholine → {3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-yl}-morpholin-4-yl-methanone

Participants

Reaction Steps

A solution of 3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-carboxylic acid (0.2 g, 0.50 mmol), morpholine (0.04 mL, 0.47 mmol) and N,N diisopropylethyl amine (0.1 mL, 0.5 mmol) in CH2Cl2 (5 mL) is treated with benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.20 g, 0.50 mmol) and stirred at room temperature overnight. The resulting mixture is diluted with CH2Cl2 (50 mL) and water (50 mL) and saturated aqueous NaCl (50 mL). The organic portion is dried over Na2SO4, filtered and concentrated. Purification by preparative TLC (8% methanol-CH2Cl2) gives {3-[2-methoxy-6-(2-methoxy-4-trifluoromethoxy-phenyl)-5-methyl-pyridin-3-yl]-3H-imidazole-4-yl}-morpholin-4-yl-methanone (Compound 6) as a white solid. TLC Rf 0.45 (elution with 8% methanol-methylene chloride).

Provenance & Evidence