Triethylamine → HCID 178454121, compound

Participants

Reaction Steps

To a round bottomed flask was added tert-butyl(cis-3-aminocyclobutyl)carbamate (0.4903 g, 2.63 mmol), 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (Intermediate 29, 0.634 g, 3.16 mmol), HATU (1.301 g, 3.42 mmol, GenScript Corp), and triethylamine (1.465 ml, 10.53 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (5.26 ml) to stir at room temperature for 24 h. 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 provide the title compound (0.8210 g, 2.226 mmol, 85% yield). LCMS showed product peak at 1.86 min (m+1=313.0, product-tbutyl group). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36 (s, 7 H) 1.49 (s, 5 H) 1.82 (qd, J=9.00, 2.35 Hz, 2 H) 2.34-2.47 (m, 2 H) 2.69 (s, 3 H) 3.48-3.65 (m, 1 H) 3.72-3.87 (m, 1 H) 7.04 (d, J=6.85 Hz, 1 H) 7.63 (d, J=6.46 Hz, 1 H) 8.42 (d, J=2.54 Hz, 1 H) 8.65 (d, J=2.35 Hz, 1 H).

Provenance & Evidence