ethyl 6-{2-[(4-aminobenzoyl)(methyl)amino]-5-methylphenoxy}hexanoate -Drug Synthesis Database

【结构式】

【分子编号】57791

【品名】ethyl 6-{2-[(4-aminobenzoyl)(methyl)amino]-5-methylphenoxy}hexanoate

【CA登记号】

【分子式】C₂₃H₃₀N₂O₄

【分子量】398.50228

【元素组成】C 69.32% H 7.59% N 7.03% O 16.06%

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：(IV)

Acylation of the anilino ester (I) with 4-nitrobenzoyl chloride (II) affords amide (III). After reduction of the 4-nitrobenzamide (III) by catalytic hydrogenation, the resultant amine (IV) is condensed with (2-ethyl-1-imidazolyl)benzoyl chloride (V) to furnish diamide (VI). Subsequent ester group saponification in (VI) gives acid (VII). This is finally coupled with N-methylpiperazine (VIII) in the presence of EDC and HOBt to produce the title compound.

参考文献中间体

合成目标

【1】 Kakefuda, A.; Kusayama, T.; Tahara, A.; Tsukamoto, S.-I.; Tsukada, J.; N-Methylbenzanilide derivatives as a novel class of selective V1A receptor antagonists. Bioorg Med Chem Lett 2002, 12, 2, 229.

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)	57789	ethyl 6-[5-methyl-2-(methylamino)phenoxy]hexanoate		C₁₆H₂₅NO₃	详情	详情
(II)	18941	p-nitrobenzoyl chloride; 4-nitrobenzoyl chloride	122-04-3	C₇H₄ClNO₃	详情	详情
(III)	57790	ethyl 6-{5-methyl-2-[methyl(4-nitrobenzoyl)amino]phenoxy}hexanoate		C₂₃H₂₈N₂O₆	详情	详情
(IV)	57791	ethyl 6-{2-[(4-aminobenzoyl)(methyl)amino]-5-methylphenoxy}hexanoate		C₂₃H₃₀N₂O₄	详情	详情
(V)	57792	2-(2-ethyl-1H-imidazol-1-yl)benzoyl chloride		C₁₂H₁₁ClN₂O	详情	详情
(VI)	57793	ethyl 6-{2-[(4-{[2-(2-ethyl-1H-imidazol-1-yl)benzoyl]amino}benzoyl)(methyl)amino]-5-methylphenoxy}hexanoate		C₃₅H₄₀N₄O₅	详情	详情
(VII)	57794	6-{2-[(4-{[2-(2-ethyl-1H-imidazol-1-yl)benzoyl]amino}benzoyl)(methyl)amino]-5-methylphenoxy}hexanoic acid		C₃₃H₃₆N₄O₅	详情	详情
(VIII)	10061	1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine	109-01-3	C₅H₁₂N₂	详情	详情

Extended Information