Naphthalic anhydride → [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester
反応式
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=O)[CH:10]=1.[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][NH2:31])[CH3:27])([CH3:19])([CH3:18])[CH3:17]>C(O)C>[C:16]([O:20][C:21](=[O:32])[NH:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][N:31]1[C:11](=[O:13])[CH:9]2[CH:10]=[CH:1][CH:2]=[C:3]3[CH:8]2[C:7](=[CH:6][CH:5]=[CH:4]3)[C:14]1=[O:15])[CH3:27])([CH3:19])([CH3:17])[CH3:18]参加物
4
実験手順
1,8-naphthalic anhydride (0.18 g, 0.9 mmol) was added to a solution of [3-[(3-aminopropyl)methylamino]propyl]carbamic acid tert-butyl ester previously prepared (Spicer at el., Bioorg. Med. Chem. 2002, vol. 10, p. 19) (0.2 g, 0.8 mmol) in absolute ethanol (20 ml). The reaction mixture was heated at reflux overnight. Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 50:1) yielded [3-[[3-(1,3-dioxo-3a,9b-dihydro-1H,3H-benzo[de]isoquinolin-2-yl)propyl]methylamino]propyl]carbamic acid tert-butyl ester (0.37 g, 90%) as a foam.