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
반응식
[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]=1참가 물질
4
반응물 1
생성물 1
시약·촉매·용매 2
실험 절차
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).