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【结 构 式】 
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【分子编号】59999 【品名】5-formyl-4-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide 【CA登记号】 |
【 分 子 式 】C13H19N3O3 【 分 子 量 】265.31228 【元素组成】C 58.85% H 7.22% N 15.84% O 18.09% |
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：(XII)Vilsmeier formylation of ethyl 4-methylpyrrole-2-carboxylate (VIII) affords aldehyde (IX). The ethyl ester group of (IX) is subsequently hydrolyzed under alkaline conditions to provide acid (X). Coupling of (X) with 4-(2-aminoethyl)morpholine (XI) gives amide (XII). Then, condensation between aldehyde (XII) and lactam (VII) in the presence of piperidine leads to adduct (XIII). The 4-chloro group of (XIII) is finally displaced with 3-chloro-4-fluoroaniline (XIV) in hot NMP to provide the title compound
| 【1】 Wei, C.C.; Tang, P.C.; McMahon, G.; Sun, L.; Hirth, K.P.; Liang, C.; Cui, J. (Sugen, Inc.); 4-Substd. 7-aza-indolin-2-ones and their use as protein kinase inhibitors. EP 1244672; WO 0146196 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 60048 | 4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one | C6H4ClN3O | 详情 | 详情 | |
| (VIII) | 60049 | ethyl 4-methyl-1H-pyrrole-2-carboxylate | C8H11NO2 | 详情 | 详情 | |
| (IX) | 60050 | ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate | C9H11NO3 | 详情 | 详情 | |
| (X) | 60051 | 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid | C7H7NO3 | 详情 | 详情 | |
| (XI) | 12880 | 4-(2-Aminoethyl)morpholine; 2-(4-Morpholinyl)ethylamine; 2-(4-Morpholinyl)-1-ethanamine; N-(2-Aminoethyl)morpholine; N-Morpholine ethanamide | 2038-03-1 | C6H14N2O | 详情 | 详情 |
| (XII) | 59999 | 5-formyl-4-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide | C13H19N3O3 | 详情 | 详情 | |
| (XIII) | 59998 | 5-[(4-chloro-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-5-ylidene)methyl]-4-methyl-N-[2-(4-morpholinyl)ethyl]-1H-pyrrole-2-carboxamide | C19H21ClN6O3 | 详情 | 详情 | |
| (XIV) | 18688 | 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline | 367-21-5 | C6H5ClFN | 详情 | 详情 |
Extended Information