4-Methylmorpholine → {(S)-1-[4-Fluoro-2-(6-fluoropyridin-3-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 4-fluoro-N2-(6-fluoropyridin-3-yl)benzene-1,2-diamine (524 mg, 2.37 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (493 mg, 2.61 mmol), HOAt (355 mg, 2.61 mmol), 4-methylmorpholine (575 μL, 5.21 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (500 mg, 2.61 mmol) in DCM (20 mL) was stirred at RT for 3 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (973 mg, quantitative). LCMS (Method C): RT 3.25 min [M+H]+ 393.3.

Provenance & Evidence