4-Chloro-1H-pyrazole -Drug Synthesis Database

【结构式】

【分子编号】14132

【品名】4-Chloro-1H-pyrazole

【CA登记号】15878-00-9

【分子式】C₃H₃ClN₂

【分子量】102.523

【元素组成】C 35.15% H 2.95% Cl 34.58% N 27.32%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Lesopitron dihydrochloride was obtained following two related procedures. 1) Reaction of 4-chloropyrazole (I) with 1,4-dibromobutane (II) gives 1-(4-bromobutyl)-4-chloropyrazole (III). Compound (III) is refluxed with 2-(1-piperazinyl)pyrimidine (IV) and potassium carbonate in DMF to give lesopitron (V), which is treated with isopropyl alcohol saturated with hydrochloric acid to pH 4.5-5 . 2) 2-(1-Piperazinyl)pyrimidine (IV) reacts with 1,4-dibromobutane (II) to yield 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane bromide (VI). The quaternary salt (VI) undergoes reaction with 4-chloropyrazole (I) in DMF in the presence of potassium carbonate to afford the free base.

参考文献中间体

合成目标

【1】 Merce-Vidal, R.; Frigola-Constansa, J.; Pares-Corominas, J. (Laboratorios del Dr. Esteve, SA); Process for the preparation of aryl (or heteroaryl) piperazinylbutylazole derivs. AU 9211429; CA 2062468; EP 0502786; ES 2036145; FR 2673628; JP 1993078313; NO 9200888; US 5227486; ZA 9201682 .
【2】 Frigola, J.; Farré, A.; Lesopitron Dihydrochloride. Drugs Fut 1994, 19, 7, 651.

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)	14132	4-Chloro-1H-pyrazole	15878-00-9	C₃H₃ClN₂	详情	详情
(II)	11883	1,4-Dibromobutane; 1,4-Butylene bromide	110-52-1	C₄H₈Br₂	详情	详情
(III)	14134	1-(4-Bromobutyl)-4-chloro-1H-pyrazole		C₇H₁₀BrClN₂	详情	详情
(IV)	11175	2-(1-Piperazinyl)pyrimidine; 2-Piperazinopyrimidine; N-(Pyrimidinyl)piperazine	20980-22-7	C₈H₁₂N₄	详情	详情
(V)	14136	2-[4-[4-(4-Chloro-1H-pyrazol-1-yl)butyl]piperazino]pyrimidine		C₁₅H₂₁ClN₆	详情	详情
(VI)	14137	8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane		C₁₂H₁₉N₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Reaction of 4-bromomethylbenzonitrile (I) with 1,2,4-triazole (II) in chloroform - acetonitrile gives 1-(4-cyanophenyl)methyl-1,2,4-triazole (III), which is treated with potassium tert-butoxide and 4-fluorobenzonitrile (IV) in DMF.

参考文献中间体

合成目标

【1】 Bowman, R.M.; Steele, R.E.; Browne, L.J. (Novartis AG); Alpha-heterocycle substd. Tolunitriles. EP 0236940; JP 1987212369 .
【2】 Graul, A.; Castaner, J.; Prous, J.; Letrozole. Drugs Fut 1994, 19, 4, 335.

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)	14132	4-Chloro-1H-pyrazole	15878-00-9	C₃H₃ClN₂	详情	详情
(I)	14200	4-(Bromomethyl)benzonitrile; alpha-Bromo-p-tolunitrile	17201-43-3	C₈H₆BrN	详情	详情
(II)	13135	1H-1,2,4-Triazole; 1,2,4-Triazole	288-88-0	C₂H₃N₃	详情	详情
(III)	14202	4-(1H-1,2,4-Triazol-1-ylmethyl)benzonitrile		C₁₀H₈N₄	详情	详情
(IV)	14144	4-Fluorobenzonitrile	1194-02-1	C₇H₄FN	详情	详情

Extended Information