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【结 构 式】 
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【分子编号】44245 【品名】N-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N-[4-(diethylamino)butyl]amine; N(1)-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N(4),N(4)-diethyl-1,4-butanediamine 【CA登记号】 |
【 分 子 式 】C16H21BrCl2N4 【 分 子 量 】420.1791 【元素组成】C 45.74% H 5.04% Br 19.02% Cl 16.88% N 13.33% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 4,5-dichloro-1,2-phenylenediamine (I) with diethyl oxalate (II) produced quinoxalinedione (III), which was brominated with PBr5 at 155 C to afford the dibromo derivative (IV). Displacement of one bromine group of (IV) with 4-(diethylamino)butylamine (V) furnished (VI). The remaining bromine of (VI) was then displaced with 5-(tributylstannyl)-2,2'-bithienyl (VII) to produce the title compound, isolated as the corresponding hydrochloride salt.
| 【1】 Li, J.J.; Yue, W.-S.; Trivedi, B.K.; et al.; Structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as potent, non-peptide interleukine-8-receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 144. |
| 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) | 18003 | 4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine | 5348-42-5 | C6H6Cl2N2 | 详情 | 详情 |
| (II) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (III) | 18007 | 6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione | 25983-13-5 | C8H4Cl2N2O2 | 详情 | 详情 |
| (IV) | 44243 | 2,3-dibromo-6,7-dichloroquinoxaline | C8H2Br2Cl2N2 | 详情 | 详情 | |
| (V) | 44244 | N-(4-aminobutyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,4-butanediamine | C8H20N2 | 详情 | 详情 | |
| (VI) | 44245 | N-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N-[4-(diethylamino)butyl]amine; N(1)-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N(4),N(4)-diethyl-1,4-butanediamine | C16H21BrCl2N4 | 详情 | 详情 | |
| (VII) | 44246 | C20H32S2Sn | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The condensation of 4,5-dichloro-1,2-phenylenediamine (I) with diethyl oxalate (II) produced quinoxalinedione (III), which was brominated with PBr5 at 155 C to afford the dibromo derivative (IV). Displacement of one bromine group of (IV) with 4-(diethylamino)butylamine (V) furnished (VI). The remaining bromine of (VI) was then displaced with 2-(tributylstannyl)benzofuran (VII) to produce the title compound.
| 【1】 Li, J.J.; Yue, W.-S.; Trivedi, B.K.; et al.; Structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as potent, non-peptide interleukine-8-receptor antagonists. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 144. |
| 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) | 18003 | 4,5-dichloro-1,2-benzenediamine; 4,5-Dichloro-o-phenylenediamine; 2-amino-4,5-dichlorophenylamine | 5348-42-5 | C6H6Cl2N2 | 详情 | 详情 |
| (II) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (III) | 18007 | 6,7-dichloro-1,4-dihydro-2,3-quinoxalinedione | 25983-13-5 | C8H4Cl2N2O2 | 详情 | 详情 |
| (IV) | 44243 | 2,3-dibromo-6,7-dichloroquinoxaline | C8H2Br2Cl2N2 | 详情 | 详情 | |
| (V) | 44244 | N-(4-aminobutyl)-N,N-diethylamine; N(1),N(1)-diethyl-1,4-butanediamine | C8H20N2 | 详情 | 详情 | |
| (VI) | 44245 | N-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N-[4-(diethylamino)butyl]amine; N(1)-(3-bromo-6,7-dichloro-2-quinoxalinyl)-N(4),N(4)-diethyl-1,4-butanediamine | C16H21BrCl2N4 | 详情 | 详情 | |
| (VII) | 44247 | 1-benzofuran-2-yl(tributyl)stannane | C20H32OSn | 详情 | 详情 |