Acetic Anhydride → 1-[(Dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate
반응식
[CH3:1][O:2][C:3]1[CH:4]=[N+:5]([O-])[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])=[C:7]2[C:12]=1[C:11](=[O:13])[N:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:9][CH2:8]2.[C:29]([O:32]C(=O)C)(=[O:31])[CH3:30]>>[C:29]([O:32][C:4]1[N:5]=[C:6]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[C:7]2[CH2:8][CH2:9][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:11](=[O:13])[C:12]=2[C:3]=1[O:2][CH3:1])(=[O:31])[CH3:30]참가 물질
3
반응 조건
- 온도
- 100 °C
실험 절차
4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide (10.3 g) was dissolved in 30 ml acetic anhydride and transferred to a 50 mL heavy walled pressure flask and sealed. The reaction was heated in a 100° C. oil bath overnight. The reaction was concentrated in vacuo. The remaining oil was dissolved in 5 mL EtOAc and purified on an Isco automated system affixed with a Biotage Flash 40 (L) (120 g silica) cartridge eluted with 0-10% MeOH in EtOAc over 20 minutes and hold at 10% for 40 minutes. The product eluted pure by HPLC/MS and NMR.