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【结 构 式】 
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【药物名称】KR-60436 【化学名称】2-[1-(4-Methoxy-2-methylphenyl)-6-(trifluoromethoxy)-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-ylamino]ethanol 【CA登记号】220853-65-6 【 分 子 式 】C22H22F3N3O3 【 分 子 量 】433.43414 |
【开发单位】Korea Res. Inst. Chem. Technol. (Originator) 【药理作用】Antiulcer Drugs, GASTROINTESTINAL DRUGS, H+/K+-ATPase Inhibitors |
合成路线1
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 |