2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol -Drug Synthesis Database

【结构式】

【分子编号】22071

【品名】2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol

【CA登记号】

【分子式】C₃₀H₂₄Cl₄N₂O₄

【分子量】618.34244

【元素组成】C 58.27% H 3.91% Cl 22.93% N 4.53% O 10.35%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

meso-1,2-Bis(2,6-dichloro-4-hydroxyphenyl)ethylenediamine (I) is svnthesized by [3.3]sigmatropic diaza-Cope rearrangement according to the method of Vögtle and Goldschmitt by reaction of meso-1,2-bis(2-hydroxyphenyl)ethylenediamine (IV) with 2,6-dichloro-4methoxybenzaldehyde (V) at temperature below 120 C via the corresponding aldimine (VI) and subsequent ether cleavage with boron tribromide.

参考文献中间体

合成目标

【1】 Vogtle, F.; Goldschmidt, E.; Chem Ber 1976, 109, 1.
【2】 Lux, F.; Hilgard, P.; Respondek, J.M.; Karl, J.; Engel, J.; Schonenberger, H.; Schumacher, W.; D-19384. Drugs Fut 1988, 13, 3, 215.

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)	22066	3,5-dichloro-4-[1,2-diamino-2-(2,6-dichloro-4-hydroxyphenyl)ethyl]phenol		C₁₄H₁₂Cl₄N₂O₂	详情	详情
(IV)	22068	2-[1,2-diamino-2-(2-hydroxyphenyl)ethyl]phenol		C₁₄H₁₆N₂O₂	详情	详情
(V)	22069	2,6-dichloro-4-methoxybenzaldehyde		C₈H₆Cl₂O₂	详情	详情
(VI)	22070	2-[[(1,2-bis(2,6-dichloro-4-methoxyphenyl)-2-[[(E)-(2-hydroxyphenyl)methylidene]amino]ethyl)imino]methyl]phenol		C₃₀H₂₄Cl₄N₂O₄	详情	详情
(VII)	22071	2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol		C₃₀H₂₄Cl₄N₂O₄	详情	详情
(VIII)	22072	1,2-bis(2,6-dichloro-4-methoxyphenyl)-1,2-ethanediamine; 2-amino-1,2-bis(2,6-dichloro-4-methoxyphenyl)ethylamine		C₁₆H₁₆Cl₄N₂O₂	详情	详情
(IX)	21351	2-Hydroxybenzaldehyde;Salicylic aldehyde；2-Formylphenol;salicylaldehyde	90-02-8	C₇H₆O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Friedel-Crafts acylation of 3-(p-methoxybenzoyl)pyrrole (I) with p-methoxybenzoyl chloride (II) gives rise to diketone (III). Subsequent alkylation of pyrrole (III) with ethyl bromoacetate (IV) in the presence of NaH and tris[(2-methoxyethoxy)ethyl]amine (TDA) furnishes the pyrrolylacetate (V). Finally, saponification of the ethyl ester group of (V) affords the target carboxylic acid.

参考文献中间体

合成目标

【1】 Nicolaou, I.; Demopoulos, V.J.; Substituted pyrrol-1-ylacetic acids that combine aldose reductase enzyme inhibitory activity and ability to prevent the nonenzymatic irreversible modification of proteins from monosaccharides. J Med Chem 2003, 46, 3, 417.

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)	64031	[4-(methyloxy)phenyl](1H-pyrrol-3-yl)methanone		C₁₂H₁₁NO₂	详情	详情
(II)	22071	2-[1,2-bis[[(E)-(2,6-dichloro-4-methoxyphenyl)methylidene]amino]-2-(2-hydroxyphenyl)ethyl]phenol		C₃₀H₂₄Cl₄N₂O₄	详情	详情
(III)	64032	[5-(4-methoxybenzoyl)-1H-pyrrol-3-yl](4-methoxyphenyl)methanone		C₂₀H₁₇NO₄	详情	详情
(IV)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(V)	64033	ethyl 2-(2,4-bis{[4-(methyloxy)phenyl]carbonyl}-1H-pyrrol-1-yl)acetate		C₂₄H₂₃NO₆	详情	详情

Extended Information