4-chloro-2,3-dimethyl-1-pyridiniumolate -Drug Synthesis Database

【结构式】

【分子编号】12815

【品名】4-chloro-2,3-dimethyl-1-pyridiniumolate

【CA登记号】

【分子式】C₇H₈ClNO

【分子量】157.59936

【元素组成】C 53.35% H 5.12% Cl 22.5% N 8.89% O 10.15%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

The condensation of 4-chloro-2,3-dimethylpyridine N-oxide (I) with 3-methoxypropanol (II) by means of NaH in DMSO gives 4-(3-methoxypropoxy)-2,3-dimethylpyridine N-oxide (III), which is treated with acetic anhydride at 90 C yielding 2-(acetoxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (IV). The hydrolysis of (IV) with NaOH in ethanol affords 2-(hydroxymethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V), which by treatment with SOCl2 in dichloromethane is converted into 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (VI). The condensation of (VI) with 2-mercaptobenzimidazole (VII) by means of NaOH in ethanol gives 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylmethylthio]benzimidazole (VIII), which is oxidized with m-chloroperbenzoic acid in ether - dichloromethane to afford 2-[4-(3-methoxypropoxy)-3-methylpyridin-2-ylsulfinyl]benzimidazole (IX). Finally, this compound is treated wtih aqueous Na2CO3.

参考文献中间体

合成目标

【1】 Souda, S.; Ueda, N.; Miyazawa, S.; Tagami, K.; Nomoto, S.; Okita, M.; Shimomura, N.; Kaneko, T.; Fujimoto, M.; Murakami, M.; Oketani, K.; Fujisaki, H.; Shibata, H.; Wakabayashi, T. (Eisai Co., Ltd.); Pyridine derivs., pharmaceutical compsns. comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same. AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445 .
【2】 Castaner, J.; Prous, J.; E-3810. Drugs Fut 1991, 16, 1, 19.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	17888	m-Chloroperbenzoic acid; 3-Chlorobenzenecarboperoxoic acid	937-14-4	C₇H₅ClO₃	详情	详情
(I)	12815	4-chloro-2,3-dimethyl-1-pyridiniumolate		C₇H₈ClNO	详情	详情
(II)	12816	3-Methoxy-1-propanol	1589-49-7	C₄H₁₀O₂	详情	详情
(III)	12817	4-(3-methoxypropoxy)-2,3-dimethyl-1-pyridiniumolate		C₁₁H₁₇NO₃	详情	详情
(IV)	12818	[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl acetate		C₁₃H₁₉NO₄	详情	详情
(V)	12819	[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methanol		C₁₁H₁₇NO₃	详情	详情
(VI)	12820	2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine; 2-(Chloromethyl)-3-methyl-4-pyridinyl 3-methoxypropyl ether	117977-20-5	C₁₁H₁₆ClNO₂	详情	详情
(VII)	12821	2-Mercaptobenzinidiazole; 1H-Benzimidazol-2-ylhydrosulfide; 1H-Benzimidazole-2-thiol; 2-Benzimidazolethiol; o-Phenylenethiourea; 2-Benzimidazolinethione; 1,3-Dihydro-2H-benzimidazole-2-thione	583-39-1	C₇H₆N₂S	详情	详情
(VIII)	12822	2-([[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfanyl)-1H-benzimidazole; 2-[(1H-Benzimidazol-2-ylsulfanyl)methyl]-3-methyl-4-pyridinyl 3-methoxypropyl ether	117977-21-6	C₁₈H₂₁N₃O₂S	详情	详情
(IX)	12823	2-([[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole; 1H-Benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide		C₁₈H₂₁N₃O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Zhong HJ．2006．Process for preparation of benzimidazole derivatives.发明专利申请公开说明书．CN 1789251(本专利属于Jiangsu Hansoh Pharmaceutical Co．Ltd，Peop Rep China)

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)	12815	4-chloro-2,3-dimethyl-1-pyridiniumolate		C₇H₈ClNO	详情	详情
(II)	66613	1H-benzo[d]imidazole-2(3H)-thione		C₇H₆N₂S	详情	详情
(III)	66614	2-(((4-chloro-3-methylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole	103312-62-5	C₁₄H₁₂ClN₃S	详情	详情
(IV)	66615	S-1H-benzo[d]imidazol-2-yl 4-chloro-3-methylpyridine-2-carbothioate		C₁₄H₁₀ClN₃OS	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Cosme Gomez A, Fau de Casa-Juana Munoz M. Gelpi Vintro JM, et aL 2001. Process for the production of 2-(2-pyridinylmethylsulfinyl)-lH-benzimidazoles. W 02001004109(本专利属于Quimica Sintetica,S A, Spain)

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)	12815	4-chloro-2,3-dimethyl-1-pyridiniumolate		C₇H₈ClNO	详情	详情
(II)	66618	4-chloro-2-(chloromethyl)-3-methylpyridine		C₇H₇Cl₂N	详情	详情
(III)	66613	1H-benzo[d]imidazole-2(3H)-thione		C₇H₆N₂S	详情	详情
(IV)	66614	2-(((4-chloro-3-methylpyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole	103312-62-5	C₁₄H₁₂ClN₃S	详情	详情
(V)	66619	2-((3-chloro-2-methylbenzyl)sulfinyl)-1H-benzo[d]imidazole		C₁₅H₁₃ClN₂OS	详情	详情

Extended Information