(E)-3-[4,6-dichloro-2-(ethoxycarbonyl)-1H-indol-3-yl]-2-propenoic acid -Drug Synthesis Database

【结构式】

【分子编号】32149

【品名】(E)-3-[4,6-dichloro-2-(ethoxycarbonyl)-1H-indol-3-yl]-2-propenoic acid

【CA登记号】

【分子式】C₁₄H₁₁Cl₂NO₄

【分子量】328.15108

【元素组成】C 51.24% H 3.38% Cl 21.61% N 4.27% O 19.5%

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：(XII)

The precursor ethyl ester (X) was also prepared from the unprotected indole carboxylic acid (XII). Conversion into amide (XIV) was carried out using activation of the carboxyl group via formation of the corresponding 2-pyridyl thioester (XIII) and then coupling with aniline (VI). Trifluoroacetic acid-promoted cleavage of the N-Boc group of (XIV) provided amine (XV). This was converted to urea (X) by means of trimethylsilyl isocyanate.

参考文献中间体

合成目标

【1】 Provera, S.; Rovatti, L.; Sabbatini, F.M.; Reggiani, A.; Di Fabio, R.; De Magistris, M.; Conti, N.; Barnaby, R.J.; Feriani, A.; Substituted analogues of GV150526 as potent glycine binding site antagonists in animal models of cerebral ischemia. J Med Chem 1999, 42, 18, 3486.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VI)	35549	tert-butyl 4-aminobenzylcarbamate	C₁₂H₁₈N₂O₂	详情	详情
(X)	35553	ethyl 3-[(E)-3-(4-[[(aminocarbonyl)amino]methyl]anilino)-3-oxo-1-propenyl]-4,6-dichloro-1H-indole-2-carboxylate	C₂₂H₂₀Cl₂N₄O₄	详情	详情
(XII)	32149	(E)-3-[4,6-dichloro-2-(ethoxycarbonyl)-1H-indol-3-yl]-2-propenoic acid	C₁₄H₁₁Cl₂NO₄	详情	详情
(XIII)	32150	ethyl 4,6-dichloro-3-[(E)-3-oxo-3-(2-pyridinylsulfanyl)-1-propenyl]-1H-indole-2-carboxylate	C₁₉H₁₄Cl₂N₂O₃S	详情	详情
(XIV)	35554	ethyl 3-[(E)-3-(4-[[(tert-butoxycarbonyl)amino]methyl]anilino)-3-oxo-1-propenyl]-4,6-dichloro-1H-indole-2-carboxylate	C₂₆H₂₇Cl₂N₃O₅	详情	详情
(XV)	35555	ethyl 3-[(E)-3-[4-(aminomethyl)anilino]-3-oxo-1-propenyl]-4,6-dichloro-1H-indole-2-carboxylate	C₂₁H₁₉Cl₂N₃O₃	详情	详情

Extended Information