【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