tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate → tert-butyl N-[(3S)-1-[(1S)-1-[6-[(2E)-2-[(7-ethoxy-6-fluoroquinolin-2-yl)methylidene]hydrazinyl]pyridin-3-yl]-2,2,2-trifluoroethyl]-3-methylpyrrolidin-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 (Example 122, Steps A and B; 5.113 g, 13.13 mmol) in ethanol (25 mL) was added 7-ethoxy-6-fluoroquinoline-2-carbaldehyde (2.878 g, 13.13 mmol) and stirred overnight at ambient temperature. The precipitate was filtered to give desired product as a pale yellow solid (5.276 g). The filtrate was subjected to chromatography (C18, 300 g, 75 mL/min, 10% MeCN/H2O to 95% MeCN over 25 column volumes) and combined with the filtered product to give tert-butyl (S)-1-((S)-1-(6-((E)-2-((7-ethoxy-6-fluoro quinolin-2-yl)methylene)hydrazinyl)pyridin-3-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ylcarbamate (6.322 g, 10.70 mmol, 81.53% yield).

Provenance & Evidence