1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole -Drug Synthesis Database

【结构式】

【分子编号】45157

【品名】1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole

【CA登记号】

【分子式】C₁₈H₂₁N₃O₃S

【分子量】359.44916

【元素组成】C 60.15% H 5.89% N 11.69% O 13.35% S 8.92%

与该中间体有关的原料药合成路线共 6 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6

合成路线1

该中间体在本合成路线中的序号：(VI)

A synthesis for [14C]-labeled E-3810 has been described: The cyclization of o-phenylenediamine (I) with [14C]-labeled carbon disulfide (II) by means of aqueous KOH gives the potassium salt of [14C]-2-mercaptobenzimidazole (III), which is treated with acetic acid to obtain the corresponding thiol (IV). The condensation of (IV) with 2-(chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine (V) by means of NaOH in refluxing ethanol yields [14C]-labeled 2-[4-(3-methoxypropoxy)-3-methylpyridin-3-ylmethylthio]benzimidazole (VI). The oxidation of (VI) with m-chloroperbenzoic acid in dichloromethane affords the corresponding sulfoxide (VIII), which is finally treated with 0.1 N NaOH in ethanol.

参考文献中间体

合成目标

【1】 Sohda, S.; Tagami, K.; Chiku, S.; Synthesis of 14C-labelled sodium pariprazole (E3810). J Label Compd Radiopharm 1993, 33, 9, 849.

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)	12824	2-Aminophenylamine; o-Phenylenediamine; 1,2-Benzenediamine	95-54-5	C₆H₈N₂	详情	详情
(III)	12825	2-Sulfanyl-1H-benzimidazole potassium salt		C₇H₅KN₂S	详情	详情
(III)	45155	1H-benzimidazol-2-ylsulfide; 1H-benzimidazole-2-thiolate		C₇H₅KN₂S	详情	详情
(IV)	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
(IV)	45156	1H-benzimidazol-2-ylhydrosulfide; 1H-benzimidazole-2-thiol		C₇H₆N₂S	详情	详情
(V)	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
(VI)	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
(VI)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	详情	详情
(VII)	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
(VII)	45158	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		C₁₈H₂₁N₃O₂S	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】 Kankan RN, Rao DR, Srinivas PL. 2004. Method for the preparation of pyridinylmethylsulfinylbenzimidazoles which are substantially free of oxidation contaminants for use in pharmaceutical compositions for treaunent of gastric ulcers．W0 2004063188(本专利属于Cipla Limited, Wain, Christopher Paul)

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)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	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】 Avrutov I, Mendelovci M, Frnkelstein N. 2004. Processes for the production of substituted 2-(2-pyridylm-etyl) sulfinyl-lH-benzimidazoles. US 2004138466
【2】 Avrutov I, Mendelovici M. 2002. Processes for the production of substituted 2-(2-pyridinylmethyl) sulfinyl-lH-benzimidazoles using tert-butyl hydmperoxide or oxone. W0 2002062786．(本专利属于Teva Pharmaceutical Industries Ltd. Israel: Teva Pharmaceutical USA, Inc)

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)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	详情	详情

合成路线4

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】 Broeckx RLM, De Smaele D, Leurs SMH. 2003. Improved process for preparing benzimidazole-type compounds, particularly antiulcer agents such as rabeprazole, by oxidation of sulfide analogs aml controlled pH alkaline extraction to remove sulfone impurities. W0 2003008406(本专利属于Janssen Pharmaceutica N, V, Belg)
【2】 Arakawa N. Kumda H.1999. Preparation of pyridinylmethylsulfinylbenzimidazoles. JP 11071370(本专利属于Eisai Co, Ltd, Japan)

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)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	详情	详情

合成路线5

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Coppi L,Berenguer MR. 2001. Method for obtaining derivativees of [[(substitmed-pyrulyl) methyl]thio] benzinudazole, useful as intermediates for omepnzole and related antiulcer agents. W0 2001079194(本专利属于Esteve Quimica, SA, 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)	19482	2,3-dimethyl-4-nitro-1-pyridiniumolate	37699-43-7	C₇H₈N₂O₃	详情	详情
(II)	66616	(3-methyl-4-nitropyridin-2-yl)methyl methanesulfonate		C₈H₁₀N₂O₅S	详情	详情
(III)	66613	1H-benzo[d]imidazole-2(3H)-thione		C₇H₆N₂S	详情	详情
(IV)	66617	2-((2-methyl-3-nitrobenzyl)thio)-1H-benzo[d]imidazole		C₁₅H₁₃N₃O₂S	详情	详情
(V)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	详情	详情

合成路线6

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】 Tagami K, Niikawa N, Kayano A. et aL. 1999. Processes for the preparation of pyridine derivatnres. WO 9902521(本专利属于Eisai Co, Ltd, Japan)

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)	45157	1H-benzimidazol-2-yl [4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl sulfoxide; 2-([[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl)-1H-benzimidazole		C₁₈H₂₁N₃O₃S	详情	详情

Extended Information