Water → 3-Methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide

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Reaction Conditions

Reaction Steps

180 mg of C-[1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropyl]-methylamine (step 1) was dissolved in 5 ml of dichloromethane and cooled to 0° C. Then 145 mg of triethylamine was added, followed by dropwise addition of a solution of 112 mg of 3-methyl-pyridine-2-carbonyl chloride in 1 ml of dichloromethane. The reaction mixture was stirred at ambient temperature for 2 hours. Then 6 ml of water were added, the resulting phases were separated and the organic phase was washed with aqueous 2N sodium hydroxide solution, then with 1N aqueous hydrochloric acid and brine, dried over sodium sulfate, filtered and concentrated. Thus, 282 mg of crude material was obtained as a brown sticky solid. This residue was purified by chromatography on silica gel, with cyclohexane/ethyl acetate (1:1) as a eluent. Thus, 104 mg of 3-methyl-pyridine-2-carboxylic acid [1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-cyclopropylmethyl]-amide was obtained as a sticky oil. 1H-NMR (CDCl3): 8.64 ppm (s, 1H), 8.35 ppm (m, 2H), 7.90 ppm (s, 1H), 7.53 ppm (m, 1H), 7.27 ppm (m, 1H), 3.74 (d, 2H), 2.60 ppm (s, 3H), 1.16 ppm (m, 2H), 1.12 ppm (m, 2H).

Provenance & Evidence