• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】54915

【品名】2-{[(6-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl}-3,5-dimethyl-4-pyridinyl methyl ether; 6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfanyl}-1H-benzimidazole

【CA登记号】

【 分 子 式 】C17H19N3O2S

【 分 子 量 】329.42288

【元素组成】C 61.98% H 5.81% N 12.76% O 9.71% S 9.73%

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:(VII)

The acetylation of 2,3,5-trimethyl-4-nitropyridine N-oxide (I) with acetic anhydride in hot acetic acid gives the 2-(acetoxymethyl)-3,5-dimethyl-4-nitropyridine (II), which, without isolation, is treated with NaOH in hot dichloromethane/water, yielding the corresponding 2-(hydroxymethyl) derivative (III). This compound, also without isolation, is treated with SOCl2 to afford 2-(chloromethyl)-3,5-dimethyl-4-nitropyridine (IV), which is condensed with 6-methoxy-1H-benzimidazole-2-thiol (V) by means of tetrabutylammonium bromide and NaOH in dichloromethane/water, providing the corresponding thioether (VI). The reaction of (VI) with sodium methoxide and K2CO3 in refluxing methanol yields 5-methoxy-2-(4-methoxy-3,5-dimethylpyridin-2-ylmethylsulfanyl)-1H-benzimidazole (VII), which is finally oxidized to the target sulfoxide with peracetic acid (VIII) in ethyl acetate.

1 Hamied, Y.K.; Kankan, R.N.; Rao, D.R. (Cipla Ltd.); Omeprazole synthesis. EP 1085019 .
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) 54909 2,3,5-trimethyl-4-nitro-1-pyridiniumolate C8H10N2O3 详情 详情
(II) 54910 (3,5-dimethyl-4-nitro-2-pyridinyl)methyl acetate C10H12N2O4 详情 详情
(III) 54911 3,5-Dimethyl-2-hydroxymethyl-4-nitropyridine C8H10N2O3 详情 详情
(IV) 54912 2-(chloromethyl)-3,5-dimethyl-4-nitropyridine C8H9ClN2O2 详情 详情
(V) 54913 6-methoxy-1H-benzimidazol-2-ylhydrosulfide; 6-methoxy-1H-benzimidazole-2-thiol C8H8N2OS 详情 详情
(VI) 54914 2-{[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfanyl}-1H-benzimidazol-6-yl methyl ether; 2-{[(3,5-dimethyl-4-nitro-2-pyridinyl)methyl]sulfanyl}-6-methoxy-1H-benzimidazole C16H16N4O3S 详情 详情
(VII) 54915 2-{[(6-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl}-3,5-dimethyl-4-pyridinyl methyl ether; 6-methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfanyl}-1H-benzimidazole C17H19N3O2S 详情 详情
(VIII) 54916 Peracetic acid; Peroxyacetic acid 79-21-0 C2H4O3 详情 详情
Extended Information