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【结 构 式】 
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【分子编号】54258 【品名】2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-4-carboxamide 【CA登记号】n/a |
【 分 子 式 】C14H16N2O2 【 分 子 量 】244.29332 【元素组成】C 68.83% H 6.6% N 11.47% O 13.1% |
合成路线1
该中间体在本合成路线中的序号：(III)The intermediate 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-amine (IV) has been obtained by two different ways: The cyclization of the bicyclic isatin (I) with cyclohexanone, NH4OH and NH4OAc in methanol gives 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-carboxamide (III), which is submitted to a Hofmann rearrangement by means of Br2 and NaOH in water to yield the intermediate amine (IV). The cyclization of 2-amino-4,5-dimethylfuran-3-carbonitrile (V) with cyclohexanone (II) by means of ZnCl2 in hot xylene or nitrobenzene gives directly the intermediate amine (IV). Finally, amine (IV) is condensed with 2-(2-oxopyrrolidin-1-yl)acetic acid methyl ester (VI) by means of NaH in NMP to provide the target amide.
| 【1】 Chaki, H.; et al.; Design and syntheses of 4-acylaminopyridine derivatives: Novel high affinity choline uptake enhancers II. Bioorg Med Chem Lett 1995, 5, 14, 1495. |
| 【2】 Ninomiya, K.; Saito, K.; Sugano, M.; Tobe, A.; Morinaka, Y.; Bessho, T.; Harada, H. (Mitsubishi Chemical Corp.); 4-Acylaminopyridine derivs.. EP 0427636; JP 1991151366; JP 1991218360; JP 1991218361; US 5397785; US 5536728; US 5861411 . |
| 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) | 54257 | 2,3-dimethyl-6,6a-dihydro-3aH-furo[2,3-b]pyrrole-4,5-dione | n/a | C8H9NO3 | 详情 | 详情 |
| (II) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (III) | 54258 | 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-4-carboxamide | n/a | C14H16N2O2 | 详情 | 详情 |
| (IV) | 54259 | 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-amine; 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-ylamine | n/a | C13H16N2O | 详情 | 详情 |
| (V) | 54260 | 2-Amino-4,5-dimethylfuran-3-carbonitrile | 5117-88-4 | C7H8N2O | 详情 | 详情 |
| (VI) | 16475 | Methyl 2-oxo-1-pyrrolidineacetate; Methyl 2-(2-oxo-1-pyrrolidinyl)acetate | 59776-88-4 | C7H11NO3 | 详情 | 详情 |