3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarbonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】48188

【品名】3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarbonyl chloride

【CA登记号】

【分子式】C₁₂H₁₃ClN₂O₅S₂

【分子量】364.8304

【元素组成】C 39.51% H 3.59% Cl 9.72% N 7.68% O 21.93% S 17.58%

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)

Coupling between 2-(methoxycarbonyl)-3-thiophenesulfonyl chloride (I) and 5-amino-3,4-dimethylisoxazole (II) afforded the corresponding sulfonamide (III). The sulfonamide NH group of (III) was then protected by reaction with bromomethyl methyl ether to produce the methoxymethyl derivative (IV). Basic hydrolysis of the methyl ester function of (IV), followed by treatment of the resultant carboxylic acid (V) with oxalyl chloride, furnished the acid chloride (VI). This was then coupled with 2'-amino-3',5'-dimethylacetophenone (VII) to yield amide (VIII). The methoxymethyl protecting group of (VIII) was finally removed by acidic treatment to provide the title compound.

参考文献中间体

合成目标

【1】 Blok, N.; Holland, G.W.; Wu, C. (Texas Biotechnology Corp.); Sulfonamides and derivs. thereof that modulate the activity of endothelin. WO 0149685 .

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)	17836	Methyl 3-(chlorosulfonyl)-2-thiophenecarboxylate; Methyl-3-chlorosulfonylthiophene-2-carboxylate		C₆H₅ClO₄S₂	详情	详情
(II)	26891	3,4-dimethyl-5-isoxazolamine	19947-75-2	C₅H₈N₂O	详情	详情
(III)	48185	methyl 3-[[(3,4-dimethyl-5-isoxazolyl)amino]sulfonyl]-2-thiophenecarboxylate		C₁₁H₁₂N₂O₅S₂	详情	详情
(IV)	48186	methyl 3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxylate		C₁₃H₁₆N₂O₆S₂	详情	详情
(V)	48187	3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxylic acid		C₁₂H₁₄N₂O₆S₂	详情	详情
(VI)	48188	3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarbonyl chloride		C₁₂H₁₃ClN₂O₅S₂	详情	详情
(VII)	47990	1-(2-amino-3,5-dimethylphenyl)-1-ethanone		C₁₀H₁₃NO	详情	详情
(VIII)	48189	N-(2-acetyl-4,6-dimethylphenyl)-3-[[(3,4-dimethyl-5-isoxazolyl)(methoxymethyl)amino]sulfonyl]-2-thiophenecarboxamide		C₂₂H₂₅N₃O₆S₂	详情	详情

Extended Information