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【结 构 式】

【分子编号】31575

【品名】4-methoxy-3,5-dimethyl-2-pyridinecarboxylic acid

【CA登记号】

【 分 子 式 】C9H11NO3

【 分 子 量 】181.19128

【元素组成】C 59.66% H 6.12% N 7.73% O 26.49%

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)

The deoxygenation of 3.5-dimethyl-4-nitropyridine N-oxide (I) gives the corresponding pyridine (II), which is treated with trimethylksilyl cyanide to yield 3,5-dimethyl-4-nitropyridine-2-carbonitrile (III). The hydrolysis of (III) affords the corresponding carboxylic acid (IV), which by a nucleophillic substitution of the NO2 group with sodium methoxide gives 4-methoxy-3,5-dimethylpyridine-2-carboxylic acid (V). The reduction of (V) with borane or LiAlH4 yields the carbinol (VI), which by reaction with SOCl2 is converted into the chloromethylpyridine (VII). The condensation of (VII) with 5-methoxy-1H-benzimidazole-2-thiol (VIII) by means of NaOH in refluxing water affords the thioether (IX), which is finally oxidized to the target sulfoxide by means of MCPBA or peracetic acid.

1 Palomo Coll, A.; Process for the preparation of 4-substd.-2-hydroxymethyl-3,5-dimethylpyridines. ES 2035767 .
2 Brandstrom, A.E. (AstraZeneca plc); Improved method for synthesis. US 5386032; WO 9118895 .
3 Heleyová, K.; Gattnar, O.; Jezek, L.; Varga, I.; Stalmach, V.; Smahovsky, V.; Oremus, V.; Zlatoidsky, P. (Slovakofarma AS); Method of omeprazole preparation. WO 9809962 .
4 Gustavsson, A.; Kallstrom, A. (AstraZeneca plc); Method for the synthesis of a benzimidazole cpd.. JP 2000502101; WO 9722603 .
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) 27246 3,5-dimethyl-4-nitro-1-pyridiniumolate C7H8N2O3 详情 详情
(II) 31572 3,5-dimethyl-4-nitropyridine C7H8N2O2 详情 详情
(III) 31573 3,5-dimethyl-4-nitro-2-pyridinecarbonitrile C8H7N3O2 详情 详情
(IV) 31574 3,5-dimethyl-4-nitro-2-pyridinecarboxylic acid C8H8N2O4 详情 详情
(V) 31575 4-methoxy-3,5-dimethyl-2-pyridinecarboxylic acid C9H11NO3 详情 详情
(VI) 18785 (4-methoxy-3,5-dimethyl-2-pyridinyl)methanol C9H13NO2 详情 详情
(VII) 16521 2-(chloromethyl)-3,5-dimethyl-4-pyridinyl methyl ether; 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine; 2-Chloromethyl-3,5-dimethyl-4-methoxypyridine 86604-75-3 C9H12ClNO 详情 详情
(VIII) 29924 5-Methoxy-1H-benzimidazol-2-ylhydrosulfide; 2-Mercapto-5-methoxybenzimidazole; 5-Methoxy-1H-benzimidazole-2-thiol; 5-Methoxy-2-mercaptbenzimidazole; 5-Methoxy-2-Benzimidazolethiol 37052-78-1 C8H8N2OS 详情 详情
(IX) 29925 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole; 2-[[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl]-3,5-dimethyl-4-pyridinyl methyl ether 73590-85-9 C17H19N3O2S 详情 详情
Extended Information