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【结 构 式】

【分子编号】12820

【品名】2-(Chloromethyl)-4-(3-methoxypropoxy)-3-methylpyridine; 2-(Chloromethyl)-3-methyl-4-pyridinyl 3-methoxypropyl ether

【CA登记号】117977-20-5

【 分 子 式 】C11H16ClNO2

【 分 子 量 】229.70628

【元素组成】C 57.52% H 7.02% Cl 15.43% N 6.1% O 13.93%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

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.

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:(V)

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.

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
Extended Information