methyl 4-(3-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)benzoate -Drug Synthesis Database

【结构式】

【分子编号】38953

【品名】methyl 4-(3-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)benzoate

【CA登记号】

【分子式】C₁₃H₁₁F₃N₂O₂

【分子量】284.2378296

【元素组成】C 54.93% H 3.9% F 20.05% N 9.86% O 11.26%

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：(XI)

In a modified procedure, 4-fluoro-2-(trifluoromethyl)benzoic acid (V) was converted to acid chloride (VI) and then esterified with methanol to give methyl ester (X). Condensation of (X) with 3-methylpyrazole (VIII) produced a mixture of regioisomeric pyrazoles (XI) and (XII) from which the major 3-methyl isomer (XI) could be isolated by either flash chromatography or by recrystallization from EtOAc-hexane. Basic hydrolysis of the methyl ester of (XI) gave acid (XIII), which was finally coupled with tricyclic amine (IV) via activation as the mixed anhydride with 2,4,6-trichlorobenzoic acid.

参考文献中间体

合成目标

【1】 Failli, A.A.; Steffan, R.J.; Sumsky, J.S.; et al.; Pyridobenzodiazepines: Synthesis and structure-activity relationship of a novel class of orally active vasopressin V2 receptor agonists. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 201.
【2】 Failli, A.A.; Shumsky, J.S.; Steffan, R.J. (American Home Products Corp.); Tricyclic vasopressin agonists. EP 1000059; WO 9906403 .

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)	38947	6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine		C₁₂H₁₁N₃	详情	详情
(V)	38951	4-fluoro-2-(trifluoromethyl)benzoic acid	141179-72-8	C₈H₄F₄O₂	详情	详情
(VI)	38948	4-fluoro-2-(trifluoromethyl)benzoyl chloride		C₈H₃ClF₄O	详情	详情
(VIII)	37998	3-methyl-1H-pyrazole	1453-58-3	C₄H₆N₂	详情	详情
(X)	38952	methyl 4-fluoro-2-(trifluoromethyl)benzoate		C₉H₆F₄O₂	详情	详情
(XI)	38953	methyl 4-(3-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)benzoate		C₁₃H₁₁F₃N₂O₂	详情	详情
(XII)	38954	methyl 4-(5-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)benzoate		C₁₃H₁₁F₃N₂O₂	详情	详情
(XIII)	38955	4-(3-methyl-1H-pyrazol-1-yl)-2-(trifluoromethyl)benzoic acid		C₁₂H₉F₃N₂O₂	详情	详情

Extended Information