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【结 构 式】 
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【分子编号】49964 【品名】methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate 【CA登记号】 |
【 分 子 式 】C34H37ClFN3O5S 【 分 子 量 】654.2021032 【元素组成】C 62.42% H 5.7% Cl 5.42% F 2.9% N 6.42% O 12.23% S 4.9% |
合成路线1
该中间体在本合成路线中的序号：(XV)Heck reaction of aryl bromide (IX) with vinyl tributyltin (X) in the presence of palladium catalyst gave the vinyl tetrahydronaphthalene (XI), which was converted to the primary alcohol (XII) by means of hydroboration with borane in THF followed by oxidative treatment with H2O2 and NaOH. Reaction of alcohol (XII) with p-toluenesulfonyl chloride and Et3N produced the corresponding tosylate (XIII) (1). This was then condensed with 6-fluoro-3-(4-piperidinyl)benzisoxazole (XIV), yielding adduct (XV). Finally, basic hydrolysis of the ester group of (XIV) provided the title carboxylic acid.
| 【1】 Cimetiere, B.; et al.; Discovery of new combined 5-HT2 and TP-receptor antagonists. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 57. |
| 【2】 Verbeuren, T.; Simonet, S.; Descombes, J.-J.; Cimetiere, B.; Lavielle, G. (ADIR et Cie.); Benzenesulfonamide derivs., process for their preparation and pharmaceutical compsns. containing them. EP 1118610; FR 2803848; JP 2001226353 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 49923 | methyl 3-(3-bromo-6-[[(4-chlorophenyl)sulfonyl]amino]-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate | C20H21BrClNO4S | 详情 | 详情 | |
| (X) | 24920 | tributyl(vinyl)stannane；Tributylvinylstannane;Vinyltributylstannane | 7486-35-3 | C14H30Sn | 详情 | 详情 |
| (XI) | 49924 | methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-3-vinyl-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate | C22H24ClNO4S | 详情 | 详情 | |
| (XII) | 49925 | methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-3-formyl-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate | C21H22ClNO5S | 详情 | 详情 | |
| (XIII) | 49926 | methyl 3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(hydroxymethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]propanoate | C21H24ClNO5S | 详情 | 详情 | |
| (XIV) | 17910 | 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole | C12H13FN2O | 详情 | 详情 | |
| (XV) | 49964 | methyl 3-(6-[[(4-chlorophenyl)sulfonyl]amino]-3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-5,6,7,8-tetrahydro-1-naphthalenyl)propanoate | C34H37ClFN3O5S | 详情 | 详情 |