1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carbonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】44131

【品名】1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carbonyl chloride

【CA登记号】

【分子式】C₁₂H₁₁ClN₂O₂

【分子量】250.68432

【元素组成】C 57.5% H 4.42% Cl 14.14% N 11.17% O 12.76%

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：(IX)

Ethyl 2,4-dioxopentanoate (V) was converted into the O-methyloxime (VI) and subsequently cyclized with 4-methoxyphenylhydrazine (VII) to furnish pyrazole (VIII) (1,2). Optionally, ester (VIII) was hydrolyzed and then converted to acid chloride (IX) by treatment with oxalyl chloride (1). Biphenylamine (IV) was coupled with ester (VIII) in the presence of trimethylaluminium (2) or, alternatively, with acid chloride (IX) (1) to give amide (X). The N-tert-butyl group of (X) was finally removed by refluxing in trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Galemmo, R.A. Jr.; Fevig, J.; Lam, P.Y.; et al.; New functional groups for interaction with the S1 pocket of factor Xa: The discovery of 1-(4-methoxyphenyl)pyrazole inhibitors. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 290.
【2】 Dominguez, C.; Fevig, J.M.; Galemmo, R.A. Jr.; Pinto, D.J.P.; Pruitt, J.R.; lma, P.; Quan, M.L.; Han, Q. (DuPont Pharmaceuticals Co.); Inhibitors of factor Xa with a neutral P1 specificity group. US 5998424; WO 9857937 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	23363	4'-amino-N-(tert-butyl)[1,1'-biphenyl]-2-sulfonamide		C₁₆H₂₀N₂O₂S	详情	详情
(V)	42500	ethyl 2,4-dioxopentanoate	615-79-2	C₇H₁₀O₄	详情	详情
(VI)	44129	ethyl 2-(methoxyimino)-4-oxopentanoate		C₈H₁₃NO₄	详情	详情
(VII)	12688	4-Hydrazinophenyl methyl ether; 1-(4-Methoxyphenyl)hydrazine	3471-32-7	C₇H₁₀N₂O	详情	详情
(VIII)	44130	ethyl 1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylate		C₁₄H₁₆N₂O₃	详情	详情
(IX)	44131	1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carbonyl chloride		C₁₂H₁₁ClN₂O₂	详情	详情
(X)	44132	N-[2'-[(tert-butylamino)sulfonyl][1,1'-biphenyl]-4-yl]-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxamide		C₂₈H₃₀N₄O₄S	详情	详情

Extended Information