tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-3-methyl-1-[(1S)-2,2,2-trifluoro-1-[6-[(2E)-2-[(6-fluoro-8-methoxyquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]ethyl]pyrrolidin-3-yl]carbamate

Participants

Reaction Steps

To a solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.00 g, 2.57 mmol) in DCM (15 mL) was added 6-fluoro-8-methoxyquinoline-2-carbaldehyde (0.5269 g, 2.568 mmol) and the reaction mixture was stirred at ambient temperature overnight. The reaction was concentrated under reduced pressure and the residue purified by chromatography (C18, 300 g, 10% MeCN/water to 95% MeCN/water over 25 column volumes) to give tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-((E)-2-((6-fluoro-8-methoxyquinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (1.132 g, 1.963 mmol, 76.45% yield).

Provenance & Evidence