Sodium Hydroxide → (6-Chloro-5-cyclopropylmethoxy-pyridin-2-yl)-(2,2-dimethyl-pyrrolidin-1-yl)-methanone

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The mixture of 6-cyclopropylmethoxy-5-trifluoromethoxy-pyridine-2-carboxylic acid and 6-chloro-5-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 47 a, 50 mg, 180 μmol) was dissolved in DMF (2 mL). TBTU (63.7 mg, 198 μmol), DIEA (154 μl, 902 μmol) and 2,2-dimethylpyrrolidine (CAN 35018-15-6, 24 μl, 198 μmol) were added and the reaction mixture was stirred at room temperature for 16 hours. Ethyl acetate (3 mL) and 1 N sodium hydroxide solution (2 mL) were added; the mixture was dried by passage through ChemElut® and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, ethyl acetate/n-heptane gradient) to give the title compound (17 mg, 31%) as off-white wax; LC-MS (UV peak area, ESI) 97%, 309.1367 [MH+].

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