2-[{[4-(4-chlorophenoxy)phenyl]sulfonyl}(methyl)amino]-3-[(4-methyl-1-piperazinyl)methyl]benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】53019

【品名】2-[{[4-(4-chlorophenoxy)phenyl]sulfonyl}(methyl)amino]-3-[(4-methyl-1-piperazinyl)methyl]benzoic acid

【CA登记号】n/a

【分子式】C₂₆H₂₈ClN₃O₅S

【分子量】530.04424

【元素组成】C 58.92% H 5.32% Cl 6.69% N 7.93% O 15.09% S 6.05%

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：(V)

Acylation of anthranilate (I) with 4-(4-chlorophenoxy)phenylsulfonyl chloride (II) provided the sulfonamide (III). Subsequent alkylation of the sulfonamide N of (III) with iodomethane yielded the N-methyl derivative (IV). Selective ester hydrolysis of (IV) with NaOH afforded the carboxylic acid (V). This was finally converted to the target hydroxamic acid via activation with oxalyl chloride, followed by treatment with hydroxylamine.

参考文献中间体

合成目标

【1】 Du, M.T.; Chen, J.M.; Levin, J.I.; et al.; The discovery of anthranilic acid-based MMP inhibitors: Part 3: Incorporation of basic amines. Bioorg Med Chem Lett 2001, 11, 22, 2975.

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)	53016	methyl 2-amino-3-[(4-methyl-1-piperazinyl)methyl]benzoate	n/a	C₁₄H₂₁N₃O₂	详情	详情
(II)	39896	4-(4-chlorophenoxy)benzenesulfonyl chloride		C₁₂H₈Cl₂O₃S	详情	详情
(III)	53017	methyl 2-({[4-(4-chlorophenoxy)phenyl]sulfonyl}amino)-3-[(4-methyl-1-piperazinyl)methyl]benzoate	n/a	C₂₆H₂₈ClN₃O₅S	详情	详情
(IV)	53018	methyl 2-[{[4-(4-chlorophenoxy)phenyl]sulfonyl}(methyl)amino]-3-[(4-methyl-1-piperazinyl)methyl]benzoate	n/a	C₂₇H₃₀ClN₃O₅S	详情	详情
(V)	53019	2-[{[4-(4-chlorophenoxy)phenyl]sulfonyl}(methyl)amino]-3-[(4-methyl-1-piperazinyl)methyl]benzoic acid	n/a	C₂₆H₂₈ClN₃O₅S	详情	详情

Extended Information