4-chloro-N-[5-formyl-7-(3-pyridinylmethyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】19594

【品名】4-chloro-N-[5-formyl-7-(3-pyridinylmethyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide

【CA登记号】

【分子式】C₂₃H₂₁ClN₂O₃S

【分子量】440.95012

【元素组成】C 62.65% H 4.8% Cl 8.04% N 6.35% O 10.89% S 7.27%

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：(XIX)

The alcohol (XV) was oxidized with 4-benzylpyridinium dichromate to the aldehyde (XVI). 3-(Tributylstannylmethyl)pyridine (XVIII), prepared from lithiated 3-picoline (XVII) and Bu3SnCl in the presence of HMPA, was coupled to bromotetrahydronaphthalene (XVI) under palladium catalysis to provide the pyridylmethyl derivative (XIX). Wittig reaction of (XIX) with phosphorane (IX) gave acrylate (XX), which was reduced with NaBH4 and CoCl2 to the tetrahydronaphthylpropionic ester (XXI). Finally, the ester group of (XXI) was hydrolyzed with NaOH in MeOH-H2O to give the title acid.

参考文献中间体

合成目标

【1】 Cimetière, B.; Dubuffet, T.; Landras, C.; Descombes, J.J.; Simonet, S.; Verbeuren, T.J.; Lavielle, G.; New tetrahydronaphthalene derivatives as combined thromboxane receptor antagonists and thromboxane synthase inhibitors. Bioorg Med Chem Lett 1998, 8, 11, 1381.
【2】 Lavielle, G.; Dubuffet, T.; Muller, O.; Laubie, M.; Verbeuren, T.; Simonet, S.; Descombes, J.-J. (ADIR et Cie.); 1,2,3,4-Tetrahydronaphthalene, chroman and thiochroman derivs. as antithrombotic agents. CA 2118102; EP 0648741; FR 2711139; JP 1995188155 .

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)	14689	Methyl (triphenylphosphoranylidene)acetate; (methoxycarbonylmethylene)triphenylphosphorane；Methyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate	2605-67-6	C₂₁H₁₉O₂P	详情	详情
(XVI)	19591	N-(7-bromo-5-formyl-1,2,3,4-tetrahydro-2-naphthalenyl)-4-chlorobenzenesulfonamide		C₁₇H₁₅BrClNO₃S	详情	详情
(XVII)	19592	(3-pyridinylmethyl)lithium		C₆H₆LiN	详情	详情
(XVIII)	19572	3-[(tributylstannyl)methyl]pyridine		C₁₈H₃₃NSn	详情	详情
(XIX)	19594	4-chloro-N-[5-formyl-7-(3-pyridinylmethyl)-1,2,3,4-tetrahydro-2-naphthalenyl]benzenesulfonamide		C₂₃H₂₁ClN₂O₃S	详情	详情
(XX)	19595	methyl (E)-3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]-2-propenoate		C₂₆H₂₅ClN₂O₄S	详情	详情
(XXI)	19596	methyl 3-[6-[[(4-chlorophenyl)sulfonyl]amino]-3-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-1-naphthalenyl]propanoate		C₂₆H₂₇ClN₂O₄S	详情	详情

Extended Information