反应详情

A solution of 6-acetamido-4-chloro-[1,5]naphthyridine-3-carbonitrile (200 mg, 0.81 mmol), 3-bromoaniline (0.5 ml) and pyridine HCl (188 mg) in ethoxyethanol (20 ml) was heated at reflux for 3 hrs. After cooling, the solvent was removed by rotary evaporation, and the residue was cooled and made basic with NH4OH. The aqueous layer was extracted with ethyl acetate. The combined extracts were washed (brine), dried (Na2SO4), and concentrated. The residue was chromatographed (flash column, silica gel, CH2Cl2: ether: MeOH=5:2:0.5) giving the title compound as a yellow solid (229 mg, 56%). mass spectrum (electrospray, m/e): 341.8 (M+H); IR cm-1: 2215, 1628; H-NMR δ (DMSO-d6): 6.816 (2H, bs, NH2), 7.093 (1H, d, C7-H), 7.35-7.43 (3H, m), 7.567 (1H, s), 7.931 (1H, d, C8-H), 8.333 (1H, s, C2-H), 9.236 (1H, s, NH).

1. temperatureat reflux for 3 hrs
2. temperatureAfter cooling
3. customthe solvent was removed by rotary evaporation
4. temperaturethe residue was cooled
5. extractionThe aqueous layer was extracted with ethyl acetate
6. washThe combined extracts were washed (brine)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated
9. customThe residue was chromatographed (flash column, silica gel, CH2Cl2: ether: MeOH=5:2:0.5)