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【结 构 式】

【分子编号】55429

【品名】2-(4-morpholinyl)ethyl 4-nitro-1-naphthyl ether; 4-{2-[(4-nitro-1-naphthyl)oxy]ethyl}morpholine

【CA登记号】

【 分 子 式 】C16H18N2O4

【 分 子 量 】302.33

【元素组成】C 63.56% H 6% N 9.27% O 21.17%

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)

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.

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
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