2-Amino-5-chlorobenzenethiol; 2-Amino-5-chlorophenylhydrosulfide -Drug Synthesis Database

【结构式】

【分子编号】11904

【品名】2-Amino-5-chlorobenzenethiol; 2-Amino-5-chlorophenylhydrosulfide

【CA登记号】

【分子式】C₆H₆ClNS

【分子量】159.63908

【元素组成】C 45.14% H 3.79% Cl 22.21% N 8.77% S 20.09%

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：(I)

A new synthesis of TA-3090 has been published: The cyclization of 2-amino-5-chlorothiophenol (I) with trans-2,3-epoxy-3-(4-methoxyphenyl)propanoic acid methyl ester (II) by heating at 160 C gives cis-8-chloro-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzo thiazepin-4-one (III), which is submitted to optical resolution with (S)-1-(2-naphthylsulfonyl)pyrrolidine-2-carbonyl chloride. The (2S-cis)-isomer of (III) is then condensed with 2-(dimethylamino)ethyl chloride (IV) by means of K2CO3 in refluxing acetone - water, yielding (2S-cis)-8-chloro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphen yl-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one (V). Finally, this compound is acetylated with acetic anhydride in refluxing pyridine and converted into the maleate salt.

参考文献中间体

合成目标

【1】 Inoue, H.; Konda, M.; Hashiyama, T.; et al.; Synthesis of halogen-substituted 1,5-benzothiazepine derivatives and their vasodilating and hypotensive activities. J Med Chem 1991, 34, 2, 675-87.

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)	11904	2-Amino-5-chlorobenzenethiol; 2-Amino-5-chlorophenylhydrosulfide		C₆H₆ClNS	详情	详情
(II)	11905	methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate		C₁₁H₁₂O₄	详情	详情
(III)	11906	(2S,3S)-8-Chloro-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one		C₁₆H₁₄ClNO₃S	详情	详情
(IV)	11907	Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine	107-99-3	C₄H₁₀ClN	详情	详情
(V)	11908	(2S,3S)-8-Chloro-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one		C₂₀H₂₃ClN₂O₃S	详情	详情

Extended Information