ethyl 1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】43755

【品名】ethyl 1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate

【CA登记号】

【分子式】C₁₈H₂₁N₃O₃

【分子量】327.38316

【元素组成】C 66.04% H 6.47% N 12.84% O 14.66%

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：(V)

2-Cyano-3-neopentyloxyaniline (I) was diazotized with NaNO2/HCl and then reduced with SnCl2 to give hydrazine (II). The required pyrazole system (IV) was then obtained by condensation of hydrazine (II) with ethyl 2-cyano-3-ethoxyacrylate (III). Deamination of (IV) was achieved by diazotization of the amino group by means of isoamyl nitrite, with concomitant decomposition of the diazonium salt in refluxing THF to yield (V). Finally, saponification of the ethyl ester group of (V) provided the title carboxylic acid.

参考文献中间体

合成目标

【1】 Ishibuchi, S.; et al.; Synthesis and structure-activity relationships of 1-phenylpyrazoles as xanthine oxidase inhibitors. Bioorg Med Chem Lett 2001, 11, 7, 879.
【2】 Ishibuchi, S.; Morimoto, H.; Inoue, H.; Naka, Y.; Fukunari, A. (Welfide Corporation); 1-Phenylpyrazole cpds. and medicinal application thereof. EP 0936217; US 6015829; WO 9818765 .

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)	43752	5-amino-2-(neopentyloxy)benzonitrile		C₁₂H₁₆N₂O	详情	详情
(II)	43753	5-hydrazino-2-(neopentyloxy)benzonitrile		C₁₂H₁₇N₃O	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)	43754	ethyl 5-amino-1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate		C₁₈H₂₂N₄O₃	详情	详情
(V)	43755	ethyl 1-[3-cyano-4-(neopentyloxy)phenyl]-1H-pyrazole-4-carboxylate		C₁₈H₂₁N₃O₃	详情	详情

Extended Information