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【结 构 式】

【分子编号】25985

【品名】2-[(E)-(dimethylamino)methylidene]-1-(3-methoxyphenyl)-1,3-butanedione

【CA登记号】

【 分 子 式 】C14H17NO3

【 分 子 量 】247.29392

【元素组成】C 68% H 6.93% N 5.66% O 19.41%

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:(III)

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
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