反应详情

To a solution of 75 mg of 1-tert-butyl-4-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydro-1,6-naphthyridin-7-yl]-1,2,3,6-tetrahydropyridinium chloride in 3 mL of MeOH and 1 mL of EtOAc was added 35 mg of PtO2 (Adam's catalyst). The mixture was evacuated and purged with N2, then evacuated and purged with H2, then stirred under an H2 balloon for 1 h. The mixture was filtered through Celite, washing with MeOH, and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in MeOH, followed by preparative HPLC (YMC C8 19×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.05% TFA over 12 min; 20 mL/minute) to yield the title compound. Mass spectrum (ESI) 542 (M+1). 1H NMR (500 MHz, CD3OD): δ 1.40 (s, 9H); 2.04-2.20 (m, 4H); 3.00-3.12 (m, 3H); 3.68 (br d, J=12.5 Hz, 2H); □6.46 (s, 1H); 6.75 (d, J=10 Hz, 1H); 7.48-7.75 (m, 8H).

1. customThe mixture was evacuated
2. custompurged with N2
3. customevacuated
4. custompurged with H2
5. filtrationThe mixture was filtered through Celite
6. washwashing with MeOH
7. concentrationconcentrated
8. customThe residue was purified by preparative thin-layer chromatography
9. washeluting with 95:5 CH2Cl2-2M NH3 in MeOH
10. customfollowed by preparative HPLC (YMC C8 19×50 mm column; 10:90 to 90:10 v/v acetonitrile/water+0.05% TFA over 12 min; 20 mL/minute)