3-(methoxycarbonyl)-5-(1H-pyrrol-1-yl)benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】35228

【品名】3-(methoxycarbonyl)-5-(1H-pyrrol-1-yl)benzoic acid

【CA登记号】

【分子式】C₁₃H₁₁NO₄

【分子量】245.23468

【元素组成】C 63.67% H 4.52% N 5.71% O 26.1%

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)

The condensation of dimethyl 5-aminoisophthalate (I) with 2,5-dimethoxytetrahydrofuran (II) in refluxing AcOH provided the pyrrolyl derivative (III). Partial hydrolysis of (III) with methanolic KOH then gave mono ester (IV). After activation of the carboxy group of (IV) as the corresponding mixed anhydride with isobutyl chloroformate, reduction employing NaBH4 furnished alcohol (V). The ester group of (V) was then displaced with guanidine-HCl (VI) in the presence of NaOMe to yield the title benzoyl guanidine, which was isolated as the methanesulfonate salt.

参考文献中间体

合成目标

【1】 Kuno, A.; Inoue, Y.; Takasugi, H.; Mizuno, H.; Yamasaki, K. (Fujisawa Pharmaceutical Co., Ltd.); Guanidine derivs. as inhibitors of Na+/H+ exchange in cells. EP 0699185; JP 1996511243; US 5824691; WO 9426709 .

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)	35226	dimethyl 5-aminoisophthalate	99-27-4	C₁₀H₁₁NO₄	详情	详情
(II)	12132	2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether	696-59-3	C₆H₁₂O₃	详情	详情
(III)	35227	dimethyl 5-(1H-pyrrol-1-yl)isophthalate		C₁₄H₁₃NO₄	详情	详情
(IV)	35228	3-(methoxycarbonyl)-5-(1H-pyrrol-1-yl)benzoic acid		C₁₃H₁₁NO₄	详情	详情
(V)	35229	methyl 3-(hydroxymethyl)-5-(1H-pyrrol-1-yl)benzoate		C₁₃H₁₃NO₃	详情	详情
(VI)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情

Extended Information