Triethylamine → HCID 22632966, compound

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Reaction Steps

A solution of 2-cyclopropylamino-3,5-difluoro-4-pyrrolidin-1-yl-benzoic acid (Example T-3, 1.65 g, 5.85 mmol) in THF (20 mL) was reacted with carbonyldiimidazole (1.2 g, 7.31 mmol) and stirred overnight at ambient temperature. The mixture was reacted with triethylamine (1.22 mL, 8.77 mmol) and O-t-butyl hydroxylamine hydrochloride (1.10 g, 8.77 mmol) and allowed to stir for 4 hours. The mixture was quenched with H2O and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The resulting residue was dissolved in THF (15 mL), reacted with carbonyldiimidazole (2.44 g, 15.0 mmol), and heated to 100° C. in a sealed tube for 5 days. The mixture was cooled, diluted with H2O, and extracted with ethyl acetate. The organic layer was washed with H2O, dried with sodium sulfate, and concentrated. The residue was purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.52 g of the title compound as a solid.

Provenance & Evidence