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【结 构 式】

【分子编号】40007

【品名】1-(4-methoxy-2-methylphenyl)-6-(2,2,2-trifluoroethoxy)-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-c]quinolin-4-one

【CA登记号】

【 分 子 式 】C21H19F3N2O3

【 分 子 量 】404.3887496

【元素组成】C 62.37% H 4.74% F 14.09% N 6.93% O 11.87%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

Reaction of 2-chloronitrobenzene (I) with the sodium alkoxide of 2,2,2-trifluoroethanol (II) in cold THF afforded trifluoroethyl ether (III). The nitro group of (III) was then reduced by means of iron and AcOH to produce 2-(trifluoroethoxy)aniline (IV). Condensation of (IV) with diethyl (2-ethoxyethyl)malonate (V) in boiling diphenyl ether led to the furoquinolinone system (VI), and subsequent reaction of (VI) with 2-methyl-4-methoxyaniline (VII) in refluxing diethylene glycol generated the pyrroloquinolinone (VIII). Chlorination of (VIII) with POCl3 gave chloropyrroloquinoline (IX). Finally, displacement of the chlorine of (IX) by ethanolamine at 180 C yielded 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
10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(I) 15248 1-chloro-2-nitrobenzene 88-73-3 C6H4ClNO2 详情 详情
(II) 19483 2,2,2-trifluoro-1-ethanol 75-89-8 C2H3F3O 详情 详情
(III) 29562 2-nitrophenyl 2,2,2-trifluoroethyl ether; 1-nitro-2-(2,2,2-trifluoroethoxy)benzene C8H6F3NO3 详情 详情
(IV) 29563 2-(2,2,2-trifluoroethoxy)aniline; 2-(2,2,2-trifluoroethoxy)phenylamine C8H8F3NO 详情 详情
(V) 34660 diethyl 2-(2-ethoxyethyl)malonate C11H20O5 详情 详情
(VI) 34661 6-(2,2,2-trifluoroethoxy)-3,5-dihydrofuro[3,2-c]quinolin-4(2H)-one C13H10F3NO3 详情 详情
(VII) 40006 4-methoxy-2-methylphenylamine; 4-methoxy-2-methylaniline 102-50-1 C8H11NO 详情 详情
(VIII) 40007 1-(4-methoxy-2-methylphenyl)-6-(2,2,2-trifluoroethoxy)-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-c]quinolin-4-one C21H19F3N2O3 详情 详情
(IX) 40008 4-chloro-1-(4-methoxy-2-methylphenyl)-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-6-yl 2,2,2-trifluoroethyl ether; 4-chloro-1-(4-methoxy-2-methylphenyl)-6-(2,2,2-trifluoroethoxy)-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline C21H18ClF3N2O2 详情 详情
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