ethyl 2-amino-4,5-dimethoxybenzoate -Drug Synthesis Database

【结构式】

【分子编号】47630

【品名】ethyl 2-amino-4,5-dimethoxybenzoate

【CA登记号】

【分子式】C₁₁H₁₅NO₄

【分子量】225.24444

【元素组成】C 58.66% H 6.71% N 6.22% O 28.41%

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：(I)

Treatment of substituted aminobenzoate (I) with 4-nitrobenzoyl chloride (II) affords amide (III), whose nitro group is converted into an amino group by hydrogenation over Pd/C, providing compound (IV). Finally, reaction of aniline (IV) with isocyanate (V) furnishes the target product.

参考文献中间体

合成目标

【1】 Hayashi, H.; Goto, Y.; Isobe, Y.; Misawa, S.; Ogita, H.; Sekine, R.; Takaku, H.; Synthesis and structure-activity relationship of inhibitor on smooth muscle cell proliferation induced by PDGF. 19th Symp Med Chem (Nov 17 1999, Tokyo) 1999, Abst 1P-03.

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)	47630	ethyl 2-amino-4,5-dimethoxybenzoate		C₁₁H₁₅NO₄	详情	详情
(II)	18941	p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride	122-04-3	C₇H₄ClNO₃	详情	详情
(III)	47631	ethyl 4,5-dimethoxy-2-[(4-nitrobenzoyl)amino]benzoate		C₁₈H₁₈N₂O₇	详情	详情
(IV)	47632	ethyl 2-[(4-aminobenzoyl)amino]-4,5-dimethoxybenzoate		C₁₈H₂₀N₂O₅	详情	详情
(V)	47633	4-isocyanatoaniline; 4-isocyanatophenylamine		C₇H₆N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Treatment of 4,5-dimethoxy-2-nitro benzoic acid (I) with H2SO4 in EtOH allows formation of the corresponding ethyl ester (II), the nitro group of which is then reduced by hydrogenation over Pd/C in EtOH to provide substituted aniline (III). Finally, the desired product is obtained by condensation of (III) with acid chloride (IV) in CH2Cl2 by means of Et3N (acid chloride (IV) can be obtained by treatment of the corresponding benzoic acid (V) with SOCl2 in refluxing chloroform).

参考文献中间体

合成目标

【1】 Isobe, Y.; Misawa, S.; Hayashi, H.; Ogita, H.; Takaku, H.; Sekine, R.; Goto, Y.; Synthesis and structure-activity relationship of diarylamide derivatives as selective inhibitors of the proliferation of human coronary artery smooth muscle cells. Bioorg Med Chem Lett 2001, 11, 4, 549.

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)	31789	4,5-dimethoxy-2-nitrobenzoic acid	4998-07-6	C₉H₉NO₆	详情	详情
(II)	50082	ethyl 4,5-dimethoxy-2-nitrobenzoate		C₁₁H₁₃NO₆	详情	详情
(III)	47630	ethyl 2-amino-4,5-dimethoxybenzoate		C₁₁H₁₅NO₄	详情	详情
(IV)	13571	3,4,5Ttrimethoxybenzoyl chloride	4521-61-3	C₁₀H₁₁ClO₄	详情	详情
(V)	32225	3,4,5-trimethoxybenzoic acid	118-41-2	C₁₀H₁₂O₅	详情	详情

Extended Information