Triethylamine → HCID 21094222, compound

Participants

Reaction Steps

NEt3 (278 μL, 2.0 mmol) and tert-butyl piperazine-1-carboxylate (373 mg, 2.0 mmol) were added to a stirred solution of 4-[1-(5-chlorothiazol-2-ylcarbamoyl)-2-(tetrahydropyran-4-yl)ethyl]benzenesulfonyl chloride (Preparation 60, 449 mg, 1.0 mmol) in anhydrous DMAc (4 mL). The mixture was stirred for 16 h, then the solvents were removed in vacuo. The residue was dissolved in EtOAc (50 mL) to give a solution that was washed with H2O (15 mL), saturated aqueous Na2CO3 (15 mL), and brine (15 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 7:3 to 1:1) gave tert-butyl 4-{4-[1-(5-chlorothiazol-2-ylcarbamoyl)-2-(tetrahydropyran-4-yl)ethyl]benzenesulfonyl}piperazine-1-carboxylate: m/z (ES+)=599.5 [M+H]+. A solution of this compound (189 mg, 316 μmol) in CH2Cl2-TFA (1:1, 7 mL) was stirred for 1 h. The solvents were evaporated off under reduced pressure, then the residue was triturated with Et2O. The product was collected, washed with Et2O, and air-dried to furnish the trifluoroacetate salt of the title compound: RTA=2.64 min; m/z (ES+)=499.3 [M+H]+.

Provenance & Evidence