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【结 构 式】 
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【分子编号】17994 【品名】3-[(E)-3-(dimethylamino)-2-propenoyl]benzonitrile 【CA登记号】 |
【 分 子 式 】C12H12N2O 【 分 子 量 】200.24016 【元素组成】C 71.98% H 6.04% N 13.99% O 7.99% |
合成路线1
该中间体在本合成路线中的序号：(III)Condensation of 3-acetylbenzonitrile (I) with N,N-dimethylformamide dimethylacetal (II) at 90 C provided enaminoketone (III). Reaction of (III) with hydrazine acetate in methanol generated pyrazole (IV), and then, reduction of nitrile group with Raney Nickel in aqueous formic acid gave aldehyde (V). Condensation of this aldehyde with benzylamine (VI) in refluxing toluene, followed by reduction of the intermediate imine (VII) with ethanolic NaBH4 yielded secondary amine (VIII). Finally, the target urea was obtained by condensation of amine (VIII) with phenyl N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]carbamate in the presence of triethylamine.
| 【1】 Tanaka, A.; et al.; Inhibitors of acyl-CoA:cholesterol O-acyltransferase. 2. Identification and structure-activity relationships of a novel series of N-alkyl-N-(heteroaryl-substituted benzyl)-N'-arylureas. J Med Chem 1998, 41, 12, 2390-2410. |
| 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) | 17992 | m-Cyanoacetophenone; 3-acetylbenzonitrile | 6136-68-1 | C9H7NO | 详情 | 详情 |
| (III) | 17994 | 3-[(E)-3-(dimethylamino)-2-propenoyl]benzonitrile | C12H12N2O | 详情 | 详情 | |
| (IV) | 17995 | 3-(1H-pyrazol-5-yl)benzonitrile | C10H7N3 | 详情 | 详情 | |
| (V) | 17996 | 3-(1H-pyrazol-5-yl)benzaldehyde | C10H8N2O | 详情 | 详情 | |
| (VII) | 17998 | N-benzyl-N-[(E)-[3-(1H-pyrazol-5-yl)phenyl]methylidene]amine; phenyl-N-[(E)-[3-(1H-pyrazol-5-yl)phenyl]methylidene]methanamine | C17H15N3 | 详情 | 详情 | |
| (VIII) | 17999 | N-benzyl[3-(1H-pyrazol-5-yl)phenyl]methanamine; N-benzyl-N-[3-(1H-pyrazol-5-yl)benzyl]amine | C17H17N3 | 详情 | 详情 | |
| (IX) | 18000 | phenyl 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylcarbamate | C15H16N2O2S2 | 详情 | 详情 |