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【结 构 式】 
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【分子编号】55385 【品名】N-{2-[(2-aminoethyl)amino]ethyl}-3-[(4-methyl-1-piperazinyl)carbonyl]-5-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide 【CA登记号】 |
【 分 子 式 】C29H31N7O6 【 分 子 量 】573.60872 【元素组成】C 60.72% H 5.45% N 17.09% O 16.74% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The condensation of 3-aminobenzoic acid (I) with 3-nitro-1,8-naphthalic anhydride (II) in hot DMSO/pyridine gives the corresponding cyclic naphthalmide (III), which is condensed with diethylenetriamine (IV) by means of CDI in DMF to yield the benzamide (V). The reaction of (V) with CDI in DMF affords the imidazolylcarbonyl derivative (VI), which is condensed with 1-methylpiperazine (VII) in THF to provide the piperazinocarbonyl compound (VIII). Finally, the amino group of (VIII) is condensed with 3-nitro-1,8-naphthalic anhydride (II) in DMSO/pyridine to give the target bis-cyclic imide.
| 【1】 Suzuki, K.; Yamada, Y.; Asao, T.; Noguchi, K.; Wakida, M. (Taiho Pharmaceutical Co., Ltd.); Naphthalimidobenzamide derivs.. EP 1020446; US 6300331; WO 0001672 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 26638 | 3-Aminobenzoic acid | 99-05-8 | C7H7NO2 | 详情 | 详情 |
| (II) | 15864 | 5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride | 3027-38-1 | C12H5NO5 | 详情 | 详情 |
| (III) | 55382 | 3-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzoic acid | C19H10N2O6 | 详情 | 详情 | |
| (IV) | 55379 | 2,2'-Diaminodiethylamine; 2,2'-Iminodiethylamine; Bis(beta-Aminoethyl)amine; Diethylentriamine; N-(2-Aminoethyl)-1,2-ethanediamine | 111-40-0 | C4H13N3 | 详情 | 详情 |
| (V) | 55383 | N-{2-[(2-aminoethyl)amino]ethyl}-3-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide | C23H21N5O5 | 详情 | 详情 | |
| (VI) | 55384 | N-{2-[(2-aminoethyl)amino]ethyl}-3-(1H-imidazol-1-ylcarbonyl)-5-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide | C27H23N7O6 | 详情 | 详情 | |
| (VII) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (VIII) | 55385 | N-{2-[(2-aminoethyl)amino]ethyl}-3-[(4-methyl-1-piperazinyl)carbonyl]-5-[5-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]benzamide | C29H31N7O6 | 详情 | 详情 |