Triethylamine → HCID 178454575, compound

Participants

Reaction Steps

To a round bottomed flask was added cis-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (Intermediate 32, 0.3010 g, 1.030 mmol), 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (Intermediate 29, 0.248 g, 1.236 mmol), HATU (0.509 g, 1.339 mmol, GenScript Corp), and triethylamine (0.573 ml, 4.12 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (2.060 ml) to stir at room temperature for 4 hours. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic extract was washed with water, saturated NaHCO3, saturated NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product (592.4 mg) 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 (0.3181 g, 0.791 mmol, 77% yield). LCMS showed product peak at 1.536 min (m+1=401.9). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (s, 4 H) 1.88-2.03 (m, 1 H) 2.60-2.69 (m, 1 H) 3.87-4.03 (m, 1 H) 6.97-7.07 (m, 1 H) 7.18-7.26 (m, 1 H) 7.39 (d, J=7.43 Hz, 1 H) 7.63-7.71 (m, 1 H) 7.76 (d, J=6.65 Hz, 1 H) 8.27 (d, J=6.26 Hz, 1 H) 8.45 (d, J=2.54 Hz, 1 H) 8.68 (d, J=2.54 Hz, 1 H)

Provenance & Evidence