2,2,2-trichloroethyl 3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】55426

【品名】2,2,2-trichloroethyl 3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-ylcarbamate

【CA登记号】

【分子式】C₁₇H₂₀Cl₃N₃O₂

【分子量】404.72292

【元素组成】C 50.45% H 4.98% Cl 26.28% N 10.38% O 7.91%

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)

The cyclization of 4-methylphenylhydrazine (I) with pivaloylacetonitrile (II) in refluxing methanol gives the aminopyrazole (III), which is treated with Troc-Cl and NaOH in water/ethyl acetate to yield the carbamate (IV). Finally, this compound is condensed with 4-[2-(4-morpholinyl)ethoxy]naphthalene-1-amine (V) by means of DIEA in hot DMSO to afford the target urea. The intermediate 4-[2-(4-morpholinyl)ethoxy]naphthalene-1-amine (V) is obtained by condensation of 2-(4-morpholinyl)ethanol (VI) with 4-nitro-1-naphthol (VII) by means of NaOH and K2CO3 in hot 1-methyl-2-pyrrolidone to yield the corresponding ether (VIII), which is finally reduced with H2 over Pd/C in methanol.

参考文献中间体

合成目标

【1】 Zhang, L.-H.; Zhu, L. (Boehringer Ingelheim Pharmaceuticals Inc.); Novel process for synthesis of heteroaryl-substd. urea cpds.. WO 0104115 .

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)	20387	1-(4-methylphenyl)hydrazine		C₇H₁₀N₂	详情	详情
(II)	44248	4,4-dimethyl-3-oxopentanenitrile	59997-51-2	C₇H₁₁NO	详情	详情
(III)	55425	3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-amine; 3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-ylamine		C₁₄H₁₉N₃	详情	详情
(IV)	55426	2,2,2-trichloroethyl 3-(tert-butyl)-1-(4-methylphenyl)-1H-pyrazol-5-ylcarbamate		C₁₇H₂₀Cl₃N₃O₂	详情	详情
(V)	55427	4-[2-(4-morpholinyl)ethoxy]-1-naphthalenamine; 4-[2-(4-morpholinyl)ethoxy]-1-naphthylamine		C₁₆H₂₀N₂O₂	详情	详情
(VI)	12856	4-(2-Hydroxyethyl)morpholine; 2-(4-Morpholinyl)-1-ethanol; N-(2-Hydroxyethyl)morpholine	622-40-2	C₆H₁₃NO₂	详情	详情
(VII)	55428	4-nitro-1-naphthol		C₁₀H₇NO₃	详情	详情
(VIII)	55429	2-(4-morpholinyl)ethyl 4-nitro-1-naphthyl ether; 4-{2-[(4-nitro-1-naphthyl)oxy]ethyl}morpholine		C₁₆H₁₈N₂O₄	详情	详情

Extended Information