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【结 构 式】

【分子编号】49979

【品名】(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]-2-propenoic acid

【CA登记号】

【 分 子 式 】C18H13F3O4S

【 分 子 量 】382.3600296

【元素组成】C 56.54% H 3.43% F 14.91% O 16.74% S 8.39%

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:(IV)

Nucleophilic substitution of 4-fluoro-3-(trifluoromethyl)benzaldehyde (II) with 6-mercaptobenzodioxan (I) afforded the sulfanyl aldehyde (III). Knoevenagel condensation of aldehyde (III) with malonic acid furnished the cinnamic acid derivative (IV), which was subsequently converted to acid chloride (V) by treatment with oxalyl chloride. Acid chloride (V) was then coupled with ethyl nipecotate (VI), yielding amide (VII). The ethyl ester group of (VII) was finally hydrolyzed using NaOH in aqueous ethanol.

1 Pei, Z.; et al.; Discovery of potent antagonists of leukocyte function-associated antigen-1/intercellular adhesion molecule-1 interaction. 3. Maide (C-ring) structure-activity relationship and improvement of overall properties of arylthio cinnamides. J Med Chem 2001, 44, 18, 2913.
2 Lynch, J.K.; Link, J.; Zhu, G.-D.; Boyd, S.A.; Winn, M.; Pei, Z.; Gunawardana, I.W.; Liu, G.; Xin, Z.; Jae, H.-S.; Freeman, J.C.; Von Geldern, T.; Staeger, M.A. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory and immune-suppressive cpds.. US 6110922; WO 0039081 .
3 Jae, H.-S.; Pei, Z.; Staeger, M.A.; Gunawardana, I.W.; Winn, M.; Freeman, J.C.; Liu, G.; Link, J.; Boyd, S.A.; Zhu, G.-D.; Von Geldern, T.W.; Xin, Z.; Lynch, J.K.; Wang, S. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory and immune-suppressive cpds.. WO 0059880 .
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) 49976 2,3-dihydro-1,4-benzodioxin-6-ylhydrosulfide; 2,3-dihydro-1,4-benzodioxine-6-thiol C8H8O2S 详情 详情
(II) 49977 alpha,alpha,alpha,4-Tetrafluoro-m-tolualdehyde; 4-Fluoro-3-(trifluoromethyl)benzaldehyde 67515-60-0 C8H4F4O 详情 详情
(III) 49978 4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)benzaldehyde C16H11F3O3S 详情 详情
(IV) 49979 (E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]-2-propenoic acid C18H13F3O4S 详情 详情
(V) 49980 (E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]-2-propenoyl chloride C18H12ClF3O3S 详情 详情
(VI) 25693 ethyl 3-piperidinecarboxylate 5006-62-2 C8H15NO2 详情 详情
(VII) 49981 ethyl 1-[(E)-3-[4-(2,3-dihydro-1,4-benzodioxin-6-ylsulfanyl)-3-(trifluoromethyl)phenyl]-2-propenoyl]-3-piperidinecarboxylate C26H26F3NO5S 详情 详情
Extended Information