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【结 构 式】 
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【分子编号】25988 【品名】5-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,6]naphthyridine-3-carbonitrile 【CA登记号】 |
【 分 子 式 】C16H11N3O2 【 分 子 量 】277.28236 【元素组成】C 69.31% H 4% N 15.15% O 11.54% |
合成路线1
该中间体在本合成路线中的序号：(VII)The reaction of 3-methoxybenzoylacetone (I) with dimethylformamide dimethylacetal (II) gives the dimethylaminomethylene derivative (III), which is cyclized with 2-cyanoacetamide (IV) by means of sodium ethoxide in ethanol yielding the pyridinone (V). The condensation of (V) with dimethylformamide dimethylacetal (II) affords the dimethylaminovinylpyridinone (VI), which is cyclized by means of ammonium acetate in DMF providing the 1,6-naphthyridine (VII). The hydrolysis of the cyano group of (VII) with NaOH gives the corresponding carboxylic acid (VIII), which is finally cyclized with N-hydroxyacetamidine (IX) by means of carbonydimidazole (CDI).
| 【1】 Odai, O.; et al.; Synthesis and pharmacological evaluation of novel 3-oxadiazolyl-1,6-naphthyridines as a new class of potential cognitive enhancers. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.256. |
| 【2】 Masumoto, K.; et al.; Structure-activity relationships and cognition-enhancing actions of novel 1,6-naphthyridine derivatives with benzodiazepine receptor inverse agonists activities. Symp Med Chem 1998, Abst 2-P-10. |
| 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) | 25984 | 1-(3-methoxyphenyl)-1,3-butanedione | C11H12O3 | 详情 | 详情 | |
| (II) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (III) | 25985 | 2-[(E)-(dimethylamino)methylidene]-1-(3-methoxyphenyl)-1,3-butanedione | C14H17NO3 | 详情 | 详情 | |
| (IV) | 12122 | Cyanoacetamide; 2-Cyanoacetamide | 107-91-5 | C3H4N2O | 详情 | 详情 |
| (V) | 25986 | 5-(3-methoxybenzoyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C15H12N2O3 | 详情 | 详情 | |
| (VI) | 25987 | 6-[(E)-2-(dimethylamino)ethenyl]-5-(3-methoxybenzoyl)-2-oxo-1,2-dihydro-3-pyridinecarbonitrile | C18H17N3O3 | 详情 | 详情 | |
| (VII) | 25988 | 5-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,6]naphthyridine-3-carbonitrile | C16H11N3O2 | 详情 | 详情 | |
| (VIII) | 25989 | 5-(3-methoxyphenyl)-2-oxo-1,2-dihydro[1,6]naphthyridine-3-carboxylic acid | C16H12N2O4 | 详情 | 详情 | |
| (IX) | 25990 | N-hydroxyethanimidamide | C2H6N2O | 详情 | 详情 |