methyl 3-(2,5-dichloro-3-thienyl)-5-({[2-(dimethylamino)ethyl]amino}carbonyl)benzoate -Drug Synthesis Database

【结构式】

【分子编号】58215

【品名】methyl 3-(2,5-dichloro-3-thienyl)-5-({[2-(dimethylamino)ethyl]amino}carbonyl)benzoate

【CA登记号】

【分子式】C₁₇H₁₈Cl₂N₂O₃S

【分子量】401.313

【元素组成】C 50.88% H 4.52% Cl 17.67% N 6.98% O 11.96% S 7.99%

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：(VI)

Mitsunobu coupling between boronic acid (I) and 3-bromo-2,5-dichlorothiophene (II) affords the thienyl isophthalate (III). Partial hydrolysis of diester (III) using methanolic KOH gives rise to mono-acid (IV), which is further condensed with N,N-dimethyl ethylenediamine (V) to provide the amide-ester (VI). Displacement of the methyl ester function of (VI) by guanidine (VII) then produces the target acyl guanidine, which is finally converted into the corresponding dihydrochloride salt.

参考文献中间体

合成目标

【1】 Kuno, A.; Mizuno, H.; Yamasaki, K.; Inoue, Y. (Fujisawa Pharmaceutical Co., Ltd.); Benzoylguanidine derivs. as medicaments. JP 1998503770; WO 9604241 .

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)	58211	3,5-bis(methoxycarbonyl)phenylboronic acid		C₁₀H₁₁BO₆	详情	详情
(II)	58212	3-bromo-2,5-dichlorothiophene	60404-18-4	C₄HBrCl₂S	详情	详情
(III)	58213	dimethyl 5-(2,5-dichloro-3-thienyl)isophthalate		C₁₄H₁₀Cl₂O₄S	详情	详情
(IV)	58214	3-(2,5-dichloro-3-thienyl)-5-(methoxycarbonyl)benzoic acid		C₁₃H₈Cl₂O₄S	详情	详情
(V)	14881	N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine	108-00-9	C₄H₁₂N₂	详情	详情
(VI)	58215	methyl 3-(2,5-dichloro-3-thienyl)-5-({[2-(dimethylamino)ethyl]amino}carbonyl)benzoate		C₁₇H₁₈Cl₂N₂O₃S	详情	详情
(VII)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情

Extended Information