Triethylamine → HCID 90204028, compound

Participants

Reaction Steps

To a solution of 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (example 48c, 0.58 g, 2.22 mmol) in dry DMF (10 ml) was added triethylamine (270 mg, 371 μl, 2.66 mmol) and TBTU (713 mg, 2.22 mmol). The reaction mixture was stirred at room temperature for 30 minutes followed by addition of 1-(benzyloxy)-2-(5-methyl-1,2,4-oxadiazol-3-yl)propan-2-amine (example 112d, 577 mg, 2.33 mmole) and the reaction was then stirred at room temperature overnight. DMF was removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was extracted with a 2M aqueous solution of sodium carbonate and the organic phase was collected. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (805 mg, 74%) as a light yellow oil. MS (ESI, m/z): 491.5 (M+H+).

Provenance & Evidence