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【结 构 式】

【分子编号】19300

【品名】2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl 2-methyl-8-quinolinyl ether; 8-[[2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl]oxy]-2-methylquinoline

【CA登记号】

【 分 子 式 】C21H16Cl2N2O

【 分 子 量 】383.27632

【元素组成】C 65.81% H 4.21% Cl 18.5% N 7.31% O 4.17%

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:(VII)

Benzyl alcohol (I) was treated with mesyl chloride and triethylamine in CH2Cl2 at 0 C, and the resulting mesylate (II) was subsequently coupled with 2-methyl-8-hydroxyquinoline (III) in the presence of NaH to afford ether (IV). Reduction of the nitro group of (IV) with hydrazine in the presence of FeCl3 and carbon gave aniline (V). Pyrrole (VII) was then obtained by heating (V) with 2,5-dimethoxy tetrahydrofuran (VI) in AcOH. Further reaction of (VII) with chlorosulfonylisocyanate (VIII) at low temperature provided the 2-cyanopyrrole (IX). The cyano group of (IX) was reduced with LiAlH4 to give amine (X). This was finally condensed with pyridinylacrylic acid (XI) using EDC and HOBt to yield the target amide, which was isolated as the dihydrochloride salt.

1 Abe, Y.; Kayakiri, H.; Satoh, S.; Inoue, T.; Sawada, Y.; Inamura, N.; Asano, M.; Aramori, I.; Hatori, C; Sawai, H.; Oku, T.; Tanaka, H.; A novel class of orally active non-peptide bradykinin B2 receptor antagonists. 4. Discovery of novel frameworks mimicking the active conformation. J Med Chem 1998, 41, 23, 4587.
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) 18590 (2,6-dichloro-3-nitrophenyl)methanol C7H5Cl2NO3 详情 详情
(II) 19295 2,6-dichloro-3-nitrobenzyl methanesulfonate C8H7Cl2NO5S 详情 详情
(III) 18598 2-methyl-8-quinolinol 826-81-3 C10H9NO 详情 详情
(IV) 18926 (E)-3-[4-[(methylamino)carbonyl]phenyl]-2-propenoic acid C11H11NO3 详情 详情
(V) 18930 2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenylamine; 2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]aniline C17H14Cl2N2O 详情 详情
(VI) 12132 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether 696-59-3 C6H12O3 详情 详情
(VII) 19300 2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl 2-methyl-8-quinolinyl ether; 8-[[2,6-dichloro-3-(1H-pyrrol-1-yl)benzyl]oxy]-2-methylquinoline C21H16Cl2N2O 详情 详情
(VIII) 14010 ethyl 5-(2-chlorophenyl)-2-hydrazino-3,6,7,9-tetrahydro-8H-pyrido[4',3':4,5]thieno[2,3-e][1,4]diazepine-8-carboxylate C19H20ClN5O2S 详情 详情
(IX) 19302 1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrole-2-carbonitrile C22H15Cl2N3O 详情 详情
(X) 19303 [1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrol-2-yl]methanamine; [1-(2,4-dichloro-3-[[(2-methyl-8-quinolinyl)oxy]methyl]phenyl)-1H-pyrrol-2-yl]methylamine C22H19Cl2N3O 详情 详情
(XI) 19304 (E)-3-[6-(acetamido)-3-pyridinyl]-2-propenoic acid C10H10N2O3 详情 详情
Extended Information