4-Methylmorpholine → {(S)-1-[4-fluoro-2-(pyridin-2-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester

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Reaction Steps

A mixture of 4-fluoro-N2-pyridin-2-ylbenzene-1,2-diamine (241 mg, 1.19 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (247 mg, 1.30 mmol), HOAt (178 mg, 1.30 mmol), 4-methylmorpholine (0.287 mL, 2.61 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (250 mg, 1.30 mmol) in DCM (10 mL) was stirred at RT for 2 h. The reaction mixture was diluted with a saturated aqueous solution of NaHCO3 and extracted with DCM (×3). The combined organic fractions were passed through a phase separator and concentrated in vacuo to afford {(S)-1-[4-fluoro-2-(pyridin-2-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester as a pale red solid (505 mg, quantitative). LCMS (Method B): RT 2.30 min [M+H]+ 375.0.

Provenance & Evidence