反应详情

To a solution of methyl 5-bromo-3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate (0.19 g, 0.37 mmol) in MeOH (3.7 mL) was added NaOMe (60 mg, 1.1 mmol). The mixture was heated at reflux for 3 hr. Cool to rt, and dilute with EtOAc. Wash with sat. aq. NaHCO3. Dry organic extract over MgSO4, filter and concentrate. Purify by biotage MPLC (90 g column, 25% ethyl acetate/hexanes) to afford 0.15 g (73%) of ethyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}-5-methoxypyrazine-2-carboxylate as a solid: 1H NMR (CDCl3) δ 3.07–3.12, 3.25–3.31, 3.76, 4.04, 4.85–4.89, 5.68–5.76, 7.28–7.49; MS (ESI+) for C22H19Cl2N3O4 m/z 460 (M+H)+.

1. temperatureThe mixture was heated
2. temperatureat reflux for 3 hr
3. washWash with sat. aq. NaHCO3
4. extractionDry organic extract over MgSO4
5. filtrationfilter
6. concentrationconcentrate
7. customPurify by biotage MPLC (90 g column, 25% ethyl acetate/hexanes)