HCID 68157901, compound → HCID 68157902, compound

Participants

Reaction Steps

A solution of {(S)-1-[4-fluoro-2-(2-methoxyethylamino)-3-pyridin-2-yl-phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (368 mg, 0.85 mmol) in AcOH (5 mL) was heated for 16 h at 70° C. in a sealed tube. After cooling to RT, the volatiles were removed in vacuo and the resulting residue taken up in DCM (15 mL) and washed with sat. NaHCO3 (30 mL). The aqueous was further extracted with DCM (2×15 mL). The combined organic fractions were washed with brine (15 mL), dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PPC, gradient 20-75% EtOAc/cyclohexane) to afford the title compound as a white solid (239 mg, 68%). LCMS (Method C): RT 2.92 min [M+H]+ 415. 1H NMR (CDCl3, 400 MHz): δ 7.84 (1H, ddd, J=7.5, 7.5, 2.0 Hz), 7.71 (1H, dd, J=9.0, 5.0 Hz), 7.59-7.56 (1H, m), 7.38 (1H, ddd, J=7.5, 5.0, 1.5 Hz), 7.09 (1H, dd, J=10.5, 9.0 Hz), 5.29-5.19 (2H, m), 4.33-4.26 (1H, m), 3.91 (1H, ddd, J=15.0, 4.0, 4.0 Hz), 3.14-3.08 (2H, m), 3.07 (1H, s), 1.60 (3H, d, J=6.5 Hz), 1.41 (9H, s)

Provenance & Evidence