Triethylamine → HCID 77107022, compound

Participants

Reaction Steps

Trifluoromethanesulfonic anhydride (0.445 mL, 2.63 mmol) was added to a solution of 3-(6-(3-(4-chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (600 mg, 1.316 mmol) and triethylamine (0.550 mL, 3.95 mmol) in DCM (20 mL). The mixture was stirred at room temperature for 90 mins. Further portions of triethylamine (0.550 mL, 3.95 mmol) and trifluoromethanesulfonic anhydride (0.445 mL, 2.63 mmol) were added to allow the reaction to run to completion. The reaction mixture was quenched with saturated NaHCO3(aq) and extracted with DCM (3×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-80% EtOAc/hexane gave a crude material which was triturated with DCM/diethyl ether/hexane to afford the title compound.

Provenance & Evidence