Diisopropylethylamine → 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (1-ethyl-1-hydroxymethyl-propyl)-amide

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Reaction Steps

To a solution of 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c, 20 mg, 77 μmol) in DMF (1.5 mL) was added HATU (32 mg, 84 μmol) and DIPEA (15 μl, 84 μmol). The reaction mixture was stirred at roomtemperature for 20 minutes followed by addition of 2-amino-2-ethylbutan-1-ol (CAN 19792-52-0, 10 mg, 84 μmol). The reaction was stirred at room temperature overnight and was poured into 15 mL of a saturated aqueous solution of sodium bicarbonate. The solution was extracted three times with 10 mL dichloromethane. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica, eluting with a heptane/ethylacetate gradient to yield the titled compound (16 mg, 58%) as white solid. MS (ESI, m/z): 361.1 (M+H+).

Provenance & Evidence