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【结 构 式】

【分子编号】64078

【品名】N-(4-aminophenyl)-N'-(4-hydroxyphenethyl)urea

【CA登记号】

【 分 子 式 】C15H17N3O2

【 分 子 量 】271.319

【元素组成】C 66.4% H 6.32% N 15.49% O 11.79%

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)

Coupling of tyramine (I) with p-nitrophenyl isocyanate (II) affords urea (III). Subsequent nitro group reduction with H2 and Pd/C gives amine (IV). Condensation of amine (IV) with ethylene oxide (V) leads to the bis-hydroxyethyl amine (VI). This is finally chlorinated employing SOCl2 in pyridine. Alternatively, amine (IV) is subjected to reductive alkylation with chloroacetaldehyde and NaBH3CN to furnish the target bis-chloroethyl amine. (1,2)

1 Jordan, A.M.; Khan, T.H.; Malkin, H.; Osborn, H.M.I.; Synthesis and analysis of urea and carbamate prodrugs as candidates for melanocyte-directed enzyme prodrug therapy (MDEPT). Bioorg Med Chem 2002, 10, 8, 2625.
2 Riley, P.A.; Photiou, A.; Khan, T.H.; Osborn, H.M.I.; Malkin, H.; Phenylethylamine derivs. and their use in the treatment of melanoma. EP 1303481; WO 0208174 .
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) 19988 4-(2-Aminoethyl)phenol; Tyramine 51-67-2 C8H11NO 详情 详情
(II) 14909 1-isocyanato-4-nitrobenzene; 4-Nitrophenyl isocyanate 100-28-7 C7H4N2O3 详情 详情
(III) 64077 N-(4-hydroxyphenethyl)-N'-(4-nitrophenyl)urea C15H15N3O4 详情 详情
(IV) 64078 N-(4-aminophenyl)-N'-(4-hydroxyphenethyl)urea C15H17N3O2 详情 详情
(V) 10393 Oxirane; Ethylene oxide 75-21-8 C2H4O 详情 详情
(VI) 64079 N-{4-[bis(2-hydroxyethyl)amino]phenyl}-N'-(4-hydroxyphenethyl)urea C19H25N3O4 详情 详情
Extended Information