3-Aminopyridine → 5-Cyclohex-1-enyl-N-ethyl-N-isopropyl-6-(2,2,2-trifluoro-ethoxy)-nicotinamide

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Reaction Steps

5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid (15 mg, 49.8 μmol) was dissolved in DMF (5 mL) to give a light yellow solution. 3-Amino-pyridine (5.15 mg, 54.8 mmol), TBTU (24.0 mg, 74.7 μmol) and N,N-diisopropylethylamine (32.2 mg, 43.5 μA, 249 μmol) was successively added under stirring and argon to give a light brown solution. The reaction mixture was stirred for 18 h; poured into 5 mL 1N NaOH/ice water and extracted with i-propyl acetate (2×20 mL). The organic layers were combined, washed with brine (1×10 mL), dried with Na2SO4 and concentrated in vacuo to give a brown oil. The crude material was purified by preparative TLC (silica gel, 1.0 mm, n-heptane/i-propyl acetate 1:1) to give the title compound as side product (5 mg, 27%) in form of a colorless oil; LC-MS (UV peak area/ESI) 94%, 371.1936 (M+H)+.

Provenance & Evidence