Triethylamine → Benzyl (2-fluoro-4-{2-[(4-pyrrolidin-1-ylpiperidine-1-carbonyl)amino]pyridin-4-yloxy}phenyl)carbamate

Participants

Reaction Steps

To a solution of benzyl [4-(2-aminopyridin-4-yloxy)-2-fluorophenyl]carbamate (230 mg) in tetrahydrofuran (6.50 ml) was added triethylamine (0.181 ml), and then phenyl chloroformate (0.123 ml) was added dropwise thereto while stirring in an ice bath, followed by stirring for 10 min. The reaction mixture was concentrated under a reduced pressure to give a residue, to which N,N-dimethylformamide (2.0 ml) and 4-(1-pyrrolidinyl)piperidine (301 mg) were then added, followed by stirring at room temperature for 11 hrs. To the reaction mixture was added ethyl acetate (50 ml) and water (30 ml) to partition. The organic layer was washed with brine (30 ml×3), and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; heptane:ethyl acetate=1:2, ethyl acetate, then ethyl acetate:methanol=10:1) to provide the titled compound (165 mg, 47.5%) as pale yellow powder.

Provenance & Evidence