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【结 构 式】 
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【分子编号】25010 【品名】1-[[2-(dibenzylamino)-3-nitro-4-quinolinyl]amino]-2-methyl-2-propanol 【CA登记号】 |
【 分 子 式 】C27H28N4O3 【 分 子 量 】456.54448 【元素组成】C 71.03% H 6.18% N 12.27% O 10.51% |
合成路线1
该中间体在本合成路线中的序号：(VI)The esterification of 3-nitroquinoline-2,4-diol (I) with trifluoromethanesulfonic anhydride (II) gives the disulfonate (III), which is condensed with 2-hydroxyisobutylamine (IV) and triethylamine in dichloromethane, yielding the aminoquinoline (V). The reaction of (V) with dibenzylamine by means of triethylamine in refluxing toluene affords the quinolinediamine (VI), which by reduction of its nitro group with NaBH4 provides the quinolinetriamine (VII). The cyclization of (VII) with 2-ethoxyacetyl chloride (VIII) by means of p-toluenesulfonic acid in refluxing acetonitrile gives the protected imidazoquinoline (IX), which is finally deprotected by treatment with Pd/C and formic acid.
| 【1】 Graul, A.; Castañer, J.; S-28463. Drugs Fut 1999, 24, 6, 622. |
| 【2】 Gerster, J.F.; Crooks, S.L.; Lindstrom, K.J. (3M Pharmaceuticals); 1-Substd., 2-substd. 1H-imidazo[4,5-c]quinolin-4-amines. EP 0582581; JP 1994504789; US 5389640; WO 9215582 . |
| 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) | 25005 | 3-nitro-2,4-quinolinediol | C9H6N2O4 | 详情 | 详情 | |
| (II) | 25006 | 3,3-dioxo-1,3-bis(trifluoromethyl)-1lambda(6),3lambda(6)-dithioxane-1,1-dione | 358-23-6 | C2F6O5S2 | 详情 | 详情 |
| (III) | 25007 | 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]-2-quinolinyl trifluoromethanesulfonate | C11H4F6N2O8S2 | 详情 | 详情 | |
| (IV) | 25008 | 1-amino-2-methylpropan-2-ol;1-amino-2-methyl-2-propanol;1,1-Dimethylethanolamine;2-Amino-a,a-dimethylethanol;2-Hydroxy-2-methyl-1-propylamine;2-Hydroxyisobutylamine;2-Methyl-2-hydroxypropylamine;3-Amino-2-methyl-2-propanol | 2854-16-2 | C4H11NO | 详情 | 详情 |
| (V) | 25009 | 4-[(2-hydroxy-2-methylpropyl)amino]-3-nitro-2-quinolinyl trifluoromethanesulfonate | C14H14F3N3O6S | 详情 | 详情 | |
| (VI) | 25010 | 1-[[2-(dibenzylamino)-3-nitro-4-quinolinyl]amino]-2-methyl-2-propanol | C27H28N4O3 | 详情 | 详情 | |
| (VII) | 25011 | 1-[[3-amino-2-(dibenzylamino)-4-quinolinyl]amino]-2-methyl-2-propanol | C27H30N4O | 详情 | 详情 | |
| (VIII) | 25012 | 2-ethoxyacetyl chloride | C4H7ClO2 | 详情 | 详情 | |
| (IX) | 25013 | 1-[4-(dibenzylamino)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methyl-2-propanol | C31H34N4O2 | 详情 | 详情 |