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【结 构 式】 
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【分子编号】51628 【品名】4-chloro-1-(4-methoxy-2-methylphenyl)-6-(trifluoromethoxy)-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline; 4-chloro-1-(4-methoxy-2-methylphenyl)-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-6-yl trifluoromethyl ether 【CA登记号】 |
【 分 子 式 】C20H16ClF3N2O2 【 分 子 量 】408.8072296 【元素组成】C 58.76% H 3.94% Cl 8.67% F 13.94% N 6.85% O 7.83% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Diethyl malonate (I) was alkylated with 2-bromoethyl ethyl ether (II) to provide diethyl (2-ethoxyethyl)malonate (III). Subsequent condensation of malonate (III) with 2-(trifluoromethoxy)aniline (IV) in boiling diphenyl ether generated the furoquinoline derivative (V). This was then condensed with 2-methyl-4-methoxyaniline (VI) in refluxing diethylene glycol to furnish adduct (VII). Chlorination of pyrroloquinolone (VII) with phosphoryl chloride gave rise to the chloro pyrroloquinoline (VIII). The chloro group of (VIII) was finally displaced with ethanolamine (IX) at 190 C, yielding the title compound.
| 【1】 Kim, H.-J.; Kim, S.-S.; Yoo, Y.-K.; Kang, S.-K.; Cheon, H.-G.; Choi, J.-K.; Yum, E.-K. (Korea Research Institute of Chemical Technology); Pyrrolo[3,2-c]quinoline derivs. containing haloalkoxy group and pharmaceutically acceptable salts thereof. CA 2268166; EP 0966466; JP 2000504352; US 6011044; WO 9909029 . |
| 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) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (II) | 34659 | 2-bromoethyl ethyl ether; 1-bromo-2-ethoxyethane | 592-55-2 | C4H9BrO | 详情 | 详情 |
| (III) | 34660 | diethyl 2-(2-ethoxyethyl)malonate | C11H20O5 | 详情 | 详情 | |
| (IV) | 51625 | 2-trifluoromethoxyaniline; alpha,alpha,alpha-trifluoro-o-anisidine; o-trifluoromethoxyaniline | 1535-75-7 | C7H6F3NO | 详情 | 详情 |
| (V) | 51626 | 6-(trifluoromethoxy)-3,5-dihydrofuro[3,2-c]quinolin-4(2H)-one | C12H8F3NO3 | 详情 | 详情 | |
| (VI) | 40006 | 4-methoxy-2-methylphenylamine; 4-methoxy-2-methylaniline | 102-50-1 | C8H11NO | 详情 | 详情 |
| (VII) | 51627 | 1-(4-methoxy-2-methylphenyl)-6-(trifluoromethoxy)-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-c]quinolin-4-one | C20H17F3N2O3 | 详情 | 详情 | |
| (VIII) | 51628 | 4-chloro-1-(4-methoxy-2-methylphenyl)-6-(trifluoromethoxy)-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline; 4-chloro-1-(4-methoxy-2-methylphenyl)-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-6-yl trifluoromethyl ether | C20H16ClF3N2O2 | 详情 | 详情 | |
| (IX) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |