2-chloro-4-(5-methyl-1H-pyrazol-1-yl)benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】52181

【品名】2-chloro-4-(5-methyl-1H-pyrazol-1-yl)benzonitrile

【CA登记号】

【分子式】C₁₁H₈ClN₃

【分子量】217.65744

【元素组成】C 60.7% H 3.7% Cl 16.29% N 19.31%

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：(XII)

Alternatively, treatment of 2-chloro-4-fluorobenzonitrile (X) with the potassium salt of 3-methylpyrazole (VIII) in THF produces an excellent yield of a 9:1 mixture of the 2-chloro-4-(3-methylpyrazol-1-yl)benzonitrile (XI) and 2-chloro-4-(5-methylpyrazol-1-yl)benzonitrile (XII) which can be separated by fractional crystallization. Hydrolysis of the nitrile (XI) to the acid, activation as the acid chloride and acylation of the pyrrolobenzodiazepine using Hünig's base in dichloromethane yields WAY-VNA-932 which is isolated by direct crystallization.

参考文献中间体

合成目标

【1】 Caggiano, T.J.; WAY-VNA-932. Drugs Fut 2002, 27, 3, 248.
【2】 Trybulski, E.J.; Ashwell, M.A.; Molinari, A.J.; Bagli, J.F.; Chan, P.S.; Failli, A.A.; Dusza, J.P.; Albright, J.D.; Caggiano, T.J. (American Home Products Corp.); Tricyclic vasopressin agonists. EP 1000062; WO 9906409 .

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)	21084	10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine	22162-53-4	C₁₂H₁₂N₂	详情	详情
(VIII)	37998	3-methyl-1H-pyrazole	1453-58-3	C₄H₆N₂	详情	详情
(X)	43492	2-chloro-4-fluorobenzonitrile	60702-69-4	C₇H₃ClFN	详情	详情
(XI)	43493	2-chloro-4-(3-methyl-1H-pyrazol-1-yl)benzonitrile		C₁₁H₈ClN₃	详情	详情
(XII)	52181	2-chloro-4-(5-methyl-1H-pyrazol-1-yl)benzonitrile		C₁₁H₈ClN₃	详情	详情

Extended Information