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【结 构 式】 
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【分子编号】68682 【品名】Cinnamonitrile;E-3-Phenyl-2-propenenitriletrans-Cinnamonitrile 【CA登记号】1885-38-7 |
【 分 子 式 】C9H7N 【 分 子 量 】129.16132 【元素组成】C 83.69% H 5.46% N 10.84% |
合成路线1
该中间体在本合成路线中的序号：(X)Treatment of cinnamonitrile (X) with HCl in toluene/EtOH gives the O-ethyl imidate.HCl (XI), which is aminated by means of methanolic ammonia in EtOH to provide amidine (XII). Cyclization of compound (XII) with dimethylmalonate (XIII) in the presence of NaOMe in MeOH at 90 °C affords the pyrimidindione (XIV), which is chlorinated with POCl3 to generate the dichloro derivative (XV). Coupling of dichloro compound (XV) with 5-methyl-3-aminopyrazole (V) by means of NaI and DIEA in DMA at 90 °C affords the secondary amine (XVI), which is finally condensed with Nmethylpiperazine (VII) to give the free base (IX) .
| 【1】 Xiao, X.-Y., Patel, D.V., Ward, J.S., Bray, M.R., Agoston, G.E., Treston, A.M.(Miikana Therapeutics, Inc.). Substituted pyrazole compounds. EP 1928456, JP 2009510107, US 2007142368, WO 2007041358. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 68679 | 5-methyl-3-aminopyrazole;3-Amino-5-methylpyrazole;3-Methyl-1H-pyrazol-5-amine | 31230-17-8 | C4H7N3 | 详情 | 详情 |
| (VII) | 10061 | 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine | 109-01-3 | C5H12N2 | 详情 | 详情 |
| (IX) | 68681 | N-(5-methyl-1H-pyrazol-3-yl)-6-(4-methylpiperazin-1-yl)-2-styrylpyrimidin-4-amine;6-(4-Methyl-1-piperazinyl)-N-(5-methyl-1H-pyrazol-3-yl)-2-[(1E)-2-phenylethenyl]-4-pyrimidinamine | 934353-76-1 | C21H25N7 | 详情 | 详情 |
| (X) | 68682 | Cinnamonitrile;E-3-Phenyl-2-propenenitriletrans-Cinnamonitrile | 1885-38-7 | C9H7N | 详情 | 详情 |
| (XI) | 68683 | ethyl cinnamimidate hydrochloride | C11H13NO.HCl | 详情 | 详情 | |
| (XII) | 68684 | cinnamimidamide | C9H10N2 | 详情 | 详情 | |
| (XIII) | 19373 | dimethyl malonate；Methyl malonate;Propanedioic acid dimethyl ester | 108-59-8 | C5H8O4 | 详情 | 详情 |
| (XIV) | 68685 | (E)-2-styrylpyrimidine-4,6(1H,5H)-dione | C12H10N2O2 | 详情 | 详情 | |
| (XV) | 68686 | (E)-4,6-dichloro-2-styrylpyrimidine | C12H8Cl2N2 | 详情 | 详情 | |
| (XVI) | 68687 | (E)-6-chloro-N-(5-methyl-1H-pyrazol-3-yl)-2-styrylpyrimidin-4-amine | C16H14ClN5 | 详情 | 详情 |