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【结 构 式】

【分子编号】11342

【品名】5-Chloro-3-[(methylamino)sulfonyl]-2-thiophenecarboxylic acid

【CA登记号】

【 分 子 式 】C6H6ClNO4S2

【 分 子 量 】255.70268

【元素组成】C 28.18% H 2.37% Cl 13.86% N 5.48% O 25.03% S 25.08%

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)

The sulfonation of 2,5-dichlorothiophene (I) with ClSO3H -SOCl2 gives 2,5-dichlorothiophene-3-sulfonic acid chloride (II), which by reaction with methylamine in CHCl3 yields the corresponding methylamide (III). The carboxylation of (III) with butyllithium and CO2 in ether affords 5-chloro-3-(N-methylsulfamoyl)thiophene-2-carboxylic acid (IV), which is esterified with PCl5 and methanol to the methyl ester (V). The condensation of (V) with methyl iodoacetate (VI) by means of NaH in DMF gives 5-chloro-3-[N-(methoxycarbonylmethyl)-N-methylsulfamoyl]thiophene-2-carboxylic acid methyl ester (VII), which is cyclized with sodium methoxide in methanol yielding 6-chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylic acid methyl ester 1,1-dioxide (VIII). Finally, this compound is treated with 2-aminopyridine (IX) in refluxing xylene.

1 Pfister, R.; Zeller, P.; Binder, D.; Hromatka, O. (F. Hoffmann-La Roche AG); Thiazine derivs. DE 2838851 .
2 Castaner, J.; Prous, J.; Lornoxicam. Drugs Fut 1992, 17, 8, 683.
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) 11339 2,5-Dichlorothiophene 3172-52-9 C4H2Cl2S 详情 详情
(II) 11340 2,5-Dichloro-3-thiophenesulfonyl chloride; 2,5-Dichlorothiophene-3-sulphonyl chloride 56946-83-9 C4HCl3O2S2 详情 详情
(III) 11341 2,5-Dichloro-N-methyl-3-thiophenesulfonamide C5H5Cl2NO2S2 详情 详情
(IV) 11342 5-Chloro-3-[(methylamino)sulfonyl]-2-thiophenecarboxylic acid C6H6ClNO4S2 详情 详情
(V) 11343 methyl 5-chloro-3-[(methylamino)sulfonyl]-2-thiophenecarboxylate C7H8ClNO4S2 详情 详情
(VI) 11344 methyl 2-iodoacetate C3H5IO2 详情 详情
(VII) 11345 methyl 5-chloro-3-[[(2-methoxy-2-oxoethyl)(methyl)amino]sulfonyl]-2-thiophenecarboxylate C10H12ClNO6S2 详情 详情
(VIII) 11346 methyl 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate C9H8ClNO5S2 详情 详情
(IX) 11305 2-Pyridinamine; 2-Pyridinylamine; 2-Aminopyridine 504-29-0 C5H6N2 详情 详情
Extended Information