ethyl (E)-2-cyano-3-{1-methyl-2-[(E)-phenylmethylidene]hydrazino}-2-propenoate -Drug Synthesis Database

【结构式】

【分子编号】62056

【品名】ethyl (E)-2-cyano-3-{1-methyl-2-[(E)-phenylmethylidene]hydrazino}-2-propenoate

【CA登记号】

【分子式】C₁₄H₁₅N₃O₂

【分子量】257.29212

【元素组成】C 65.36% H 5.88% N 16.33% O 12.44%

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：(IV)

Benzaldehyde (I) is converted into the corresponding hydrazone (II) upon treatment with methylhydrazine in toluene. Condensation of hydrazone (II) with ethyl (ethoxymethylene)cyanoacetate (III) produces the hydrazinomethylene cyanoacetate (IV), which is further cyclized to the pyrazole (V) under acidic conditions (1). Heating of amino ester (V) with formamide gives rise to the pyrazolopyrimidinone (VI). This is finally alkylated with 2,6-difluorobenzyl chloride (VII) to furnish the title compound

参考文献中间体

合成目标

【1】 Unverferth, K.; Lankau, H-J.; Arnold, T.; Synthesis and anticonvulsant activity of AWD 34-176. Drugs Fut 2002, 27, Suppl. A.
【2】 Lankau, H.-J.; Unverferth, K.; Tober, C.; Rundfeldt, C.; Arnold, T.; Dost, R.; Gasparic, A.; Bernöster, K. (AWD.pharma GmbH & Co. KG); 2,5-Dihydro-pyrazolo[3,4-d]pyrimidin-4-ones with an anticonvulsive action and methods for producing the same. WO 0218387 .

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)	10498	Benzaldehyde;Benzoic aldehyde;Phenylmethanal	100-52-7	C₇H₆O	详情	详情
(II)	62055	benzaldehyde N-methylhydrazone		C₈H₁₀N₂	详情	详情
(III)	43563	ethyl (E)-2-cyano-3-ethoxy-2-propenoate；(E)-ethyl 2-cyano-3-ethoxyacrylate	94-05-3	C₈H₁₁NO₃	详情	详情
(IV)	62056	ethyl (E)-2-cyano-3-{1-methyl-2-[(E)-phenylmethylidene]hydrazino}-2-propenoate		C₁₄H₁₅N₃O₂	详情	详情
(V)	62057	ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylate		C₇H₁₁N₃O₂	详情	详情
(VI)	62058	2-methyl-2,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one		C₆H₆N₄O	详情	详情
(VII)	23150	2-(chloromethyl)-1,3-difluorobenzene	697-73-4	C₇H₅ClF₂	详情	详情

Extended Information