1-(chloromethyl)-3-[[6-[2-(dimethylamino)ethoxy]-5-methoxyindol-2-yl]carbonyl]-5-nitro-1,2-dihydro-3H-benz[e]indole → 5-amino-1-(chloromethyl)-3-[[6-[2-(dimethylamino)ethoxy]-5-methoxyindol-2-yl]carbonyl]-1,2-dihydro-3H-benz[e]indole
反応式
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]([N+:16]([O-])=O)=[CH:7][C:6]=2[N:5]([C:19]([C:21]2[NH:22][C:23]3[C:28]([CH:29]=2)=[CH:27][C:26]([O:30][CH3:31])=[C:25]([O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:24]=3)=[O:20])[CH2:4]1>C1COCC1.O=[Pt]=O>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[C:11]2[CH:3]([CH2:2][Cl:1])[CH2:4][N:5]([C:19]([C:21]3[NH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][C:26]([O:30][CH3:31])=[C:25]([O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:24]=4)=[O:20])[C:6]=2[CH:7]=1参加物
4
反応物 1
生成物 1
試薬・触媒・溶媒 2
実験手順
A solution of 14f (130 mg, 0.25 mmol) in THF (20 mL) was hydrogenated over PtO2 (30 mg) at 55 psi for 2 h. The catalyst was removed and the solution was concentrated under reduced pressure below 30° C. The residue was dissolved in a small volume of CH2Cl2, the solution was diluted with petroleum ether to precipitate impurities which were removed by filtration, and then further addition of petroleum ether precipitated 15f (87 mg, 71%), mp 130-133° C. 1H NMR [(CD3)2SO] δ 11.38 (d, J=1.6 Hz, 1 H, NH), 8.07 (d, J=8.5 Hz, 1 H, H-6), 7.75 (d, J=8.3 Hz, 1 H, H-9), 7.72 (s, 1 H, H-4), 7.45 (t, J=7.4 Hz, 1 H, H-8), 7.27 (t, J=7.7 hz, 1 H, H-7), 7.15 (s, 1 H, H-3'), 7.05 (s, 1 H, H-4' or 7'), 6.99 (s, 1 H, H-4' or 7'), 5.96, 5.94 (2×s, 2 H, NH2), 4.71 (dd, J=10.6, 9.1 Hz, 1 H, H-2), 4.50 (dd, J=10.9 Hz, 1.6 Hz, 1 H, H-2), 4.16-4.08 (m, 1 H, H-1), 4.05 (t, J=6.0 Hz, 2 H, OCH2), 3.98 (dd, J=11.0, 3.0 Hz, 1 H, CHHCl), 3.79 (s, 1 H, OCH3), 3.74 (dd, J=10.9, 8.2 Hz, 1 H, CHHCl), 2.68 (t, J=5.9 Hz, 2 H, OCH2CH2), 2.25 (s, 6 H, N(CH3)2).