Triethylamine → HCID 178461877, compound

Participants

Reaction Steps

A solution of di(1H-benzo[d][1,2,3]triazol-1-yl)methanethione (3.0 g, 10.7 mmol) in THF (60 mL) was treated with (S)-1-(4-fluorophenyl)ethanamine (1.49 g, 10.7 mmol). The reaction was stirred at ambient temperature for 18 h and then 1-amino-1H-pyrrole-2-carboxamide (1.33 g, 10.7 mmol) was added, followed by triethylamine (2.9 mL, 10.7 mmol). The resulting mixture was warmed to 50° C. and stirred for 16 hours. The reaction mixture was concentrated, then diluted with EtOAc (50 mL) and washed with saturated aqueous NaHCO3 (3×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2, 0% to 2% MeOH/CH2Cl2 gradient) to afford the desired compound as a solid (2.4 g, 73%). HPLC tR=2.636 min (Combiscreen ODS 4.6×50 mm, 10-90% aqueous methanol containing 0.2% H3PO4 4 min gradient, monitored at 220 nm). [M+H+]=307.33.

Provenance & Evidence