Triethylamine → HCID 178426491, compound

Participants

Reaction Steps

To a round bottomed flask was added 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (0.267 g, 1.333 mmol, 00388), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.659 g, 1.733 mmol, GenScript) and triethylamine (0.743 ml, 5.33 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (4.44 ml). cis-N1-(5-Methylpyridin-2-yl)cyclohexane-1,4-diamine (0.3709 g, 1.333 mmol) was added and the reaction was allowed to stir at room temperature for 4 h. Solvent was evaporated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane to give the title compound (105.0 mg, 0.271 mmol, 20.3% yield). Product peak was found at 1.438 min (m+1=388.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45-1.67 (m, 12 H) 1.75 (d, J=4.89 Hz, 2 H) 2.08 (s, 3 H) 3.68 (br. s., 1 H) 3.76 (br. s., 1 H) 6.50 (d, J=8.41 Hz, 1 H) 7.14-7.28 (m, 2 H) 7.76 (s, 1 H) 8.42 (d, J=2.54 Hz, 1 H) 8.65 (d, J=2.54 Hz, 1 H)

Provenance & Evidence