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【结 构 式】

【分子编号】52237

【品名】methyl 4-[3-(benzyloxy)-4-methoxyphenyl]-3-(1H-pyrrol-1-yl)-2-thiophenecarboxylate

【CA登记号】

【 分 子 式 】C24H21NO4S

【 分 子 量 】419.50108

【元素组成】C 68.72% H 5.05% N 3.34% O 15.26% S 7.64%

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:(I)

Reaction of 4-methoxyaniline (XXI) with ethyl acetoacetate (XXII) by means of triethanolamine in refluxing xylene gives the acetoacetanilide (XXIII), which is cyclized by means of hot triethanolamine and H2SO4 to yield 6-methoxy-4-methylquinolin-2(1H)-one (I), which is treated with refluxing POCl3 to provide 2-chloro-6-methoxy-4-methylquinoline (XXIV). Reaction of compound (XXIV) with SO2Cl2 in hot AcOH affords 2,5-dichloro-6-methoxy-4-methylquinoline (XXV), which is treated with MeONa in refluxing methanol to furnish 5-chloro-2,6-dimethoxy-4-methylquinoline (XXVI). Alternatively, the reaction of compound (XXIV) with MeONa as before gives 2,6-dimethoxy-4-methylquinoline (XXVII), which is treated with SO2Cl2 in hot AcOH to give the already described 5-chloro-2,6-dimethoxy-4-methylquinoline (XXVI). Nitration of compound (XXVI) with KNO3 and P2O5 gives the 8-nitroquinoline derivative (XXVIII), which is condensed with 3-(trifluoromethyl)phenol (IV) by means of KOH in hot NMP to yield the diaryl ether (VII). Finally, the nitro group of compound (VII) is reduced with hydrazine over Pd/C.

1 McIntyre, J.A.; Castaner, J.; Bayes, M.; Tafenoquine Succinate. Drugs Fut 2003, 28, 9, 859.
2 Ugwuegbulam, C.O.; Foy, J.E. (GlaxoSmithKline Inc.; GlaxoSmithKline plc); Process for the preparation of anti-malarial drugs. US 6479660; WO 9713753 .
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) 52237 methyl 4-[3-(benzyloxy)-4-methoxyphenyl]-3-(1H-pyrrol-1-yl)-2-thiophenecarboxylate C24H21NO4S 详情 详情
(IV) 33504 3-(trifluoromethyl)phenol 98-17-9 C7H5F3O 详情 详情
(VII) 57243 2,6-dimethoxy-4-methyl-8-nitro-5-quinolinyl 3-(trifluoromethyl)phenyl ether; 2,6-dimethoxy-4-methyl-8-nitro-5-[3-(trifluoromethyl)phenoxy]quinoline C19H15F3N2O5 详情 详情
(VIII) 48081 2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinamine; 2,6-dimethoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]-8-quinolinylamine C19H17F3N2O3 详情 详情
(XXI) 10478 p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine 104-94-9 C7H9NO 详情 详情
(XXII) 11819 ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate 141-97-9 C6H10O3 详情 详情
(XXIII) 52236 methyl 3-amino-4-[3-(benzyloxy)-4-methoxyphenyl]-2-thiophenecarboxylate C20H19NO4S 详情 详情
(XXIV) 52238 [4-[3-(benzyloxy)-4-methoxyphenyl]-3-(1H-pyrrol-1-yl)-2-thienyl](1-pyrrolidinyl)methanone C27H26N2O3S 详情 详情
(XXV) 57239 2,5-dichloro-4-methyl-6-quinolinyl methyl ether; 2,5-dichloro-6-methoxy-4-methylquinoline C11H9Cl2NO 详情 详情
(XXVI) 57240 5-chloro-2,6-dimethoxy-4-methylquinoline; 5-chloro-2-methoxy-4-methyl-6-quinolinyl methyl ether C12H12ClNO2 详情 详情
(XXVII) 57241 2-methoxy-4-methyl-6-quinolinyl methyl ether; 2,6-dimethoxy-4-methylquinoline C12H13NO2 详情 详情
(XXVIII) 57242 5-chloro-2,6-dimethoxy-4-methyl-8-nitroquinoline; 5-chloro-2-methoxy-4-methyl-8-nitro-6-quinolinyl methyl ether C12H11ClN2O4 详情 详情
Extended Information