Triethylamine → HCID 69101849, compound

Participants

Reaction Steps

To a round bottom flask was added triazole 24 (43.8 mg, 0.20 mmol, 1.0 eq.), DMF (2.0 mL), HOBt (29.7 mg, 0.22 mmol, 1.1 eq.), EDCI (42.0 mg, 0.22 mmol, 1.1 eq.), and triethylamine (0.076 mL, 0.60 mmol, 3.0 eq.). The reaction was stirred at RT for 30 min before adding 5-amino-2-chloro-benzotrifluoride (78.0 mg, 0.40 mmol, 2.0 eq.) and stirring overnight at RT. The reaction was quenched with water, extracted with EtOAc 3×, washed with 10% LiCl to remove DMF, dried with Na2SO4, and then concentrated via rotary evaporation. Trituration with ether gave triazole 25 in only 80% purity. Further purification by prep HPLC then gave pure triazole 25 as a white solid (21 mg, 23% yield). LC/MSD (BP Series 1100 MSD) MS (ES+) m/z 397.0 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.56 (br. s, 1H), 9.17 (s, 2H), 8.25 (d, 1H), 7.95 (dd, 1H), 7.69 (d, 1H), 7.49 (t, 1H), 7.43 (m, 1H), 7.33 (dd, 1H), 7.10 (dd, 1H), 4.84 (s, 2H) ppm.

Provenance & Evidence