5-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carbonitrile -Drug Synthesis Database

【结构式】

【分子编号】26910

【品名】5-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carbonitrile

【CA登记号】

【分子式】C₁₁H₁₆N₄

【分子量】204.275

【元素组成】C 64.68% H 7.89% N 27.43%

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：(VIII)

Reaction of triethyl orthopropionate (I) with malononitrile (II) at reflux temperature provided (1-ethoxypropylidene)malononitrile (III). Cyclopentanone (IV) was condensed with tert-butyl carbazate (V) to afford the corresponding hydrazone (VI). Subsequent reduction with sodium cyanoborohydride, followed by acid deprotection furnished cyclopentylhydrazine (VII). Then, condensation of (VII) with malononitrile derivative (III) produced pyrazole (VIII). Partial hydrolysis of the cyano group of (VIII) using concentrated sulfuric acid gave carboxamide (IX).

参考文献中间体

合成目标

【1】 Bacon, E.R.; Singh, B.; Lesher, G.Y.; Lesher, L.E. (Sanofi-Synthelabo); 6-Heterocyclyl pyrazolo[3,4-d]pyrimidin-4-ones and compsns. and method of use. US 5294612 .

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)	10395	1,1,1-Triethoxypropane; 1,1-Diethoxypropyl ethyl ether; Triethyl orthopropionate	115-80-0	C₉H₂₀O₃	详情	详情
(II)	12061	Malononitrile	109-77-3	C₃H₂N₂	详情	详情
(III)	26907	2-(1-ethoxypropylidene)malononitrile		C₈H₁₀N₂O	详情	详情
(IV)	15113	cyclopentanone	120-92-3	C₅H₈O	详情	详情
(V)	10893	tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate	870-46-2	C₅H₁₂N₂O₂	详情	详情
(VI)	26908	tert-butyl 2-cyclopentylidene-1-hydrazinecarboxylate		C₁₀H₁₈N₂O₂	详情	详情
(VII)	26909	1-cyclopentylhydrazine		C₅H₁₂N₂	详情	详情
(VIII)	26910	5-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carbonitrile		C₁₁H₁₆N₄	详情	详情
(IX)	26911	5-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide		C₁₁H₁₈N₄O	详情	详情

Extended Information