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【结 构 式】 
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【分子编号】48881 【品名】Acetoacetaldehyde Dimethylacetal; 1,1-dimethoxy-3-butanone; 3-Ketobutyraldehyde dimethyl acetal; 3-Ketobutyric aAldehyde 1-dimethylacetal; 3-Oxobutyraldehyde dimethylacetal; 4,4-Dimethoxy-2-butanone 【CA登记号】5436-21-5 |
【 分 子 式 】C6H12O3 【 分 子 量 】132.15948 【元素组成】C 54.53% H 9.15% O 36.32% |
合成路线1
该中间体在本合成路线中的序号：(III)Amination of cyclohexanedione derivative (I) with ammonium acetate in refluxing ethanol affords compound (II), which is converted into tetrahydroquinolinone derivative (IV) by condensation with 3-oxobutylaldehyde dimethylacetal (III) and cyclization by means of KOH in refluxing EtOH. The desired compound is finally obtained by first reaction of ketone (IV) with aminoguanidine hydrochloride (V) in refluxing EtOH/HCl, followed by formation of the corresponding dimethanesulfonate salt by treatment with methanesulfonic acid.
| 【1】 Fukumoto, S.; et al.; Novel, non-acylguanidine-type Na+/H+ exchanger inhibitors: Synthesis and pharmacology of 5-tetrahydroquinolinylidene aminoguanidine derivatives. J Med Chem 2002, 45, 14, 3009. |
| 【3】 Shiraishi, M.; Fukumoto, S.; Kusumoto, K. (Takeda Chemical Industries, Ltd.); Aminoguanidine hydrazone derivs., process for producing the same and drugs thereof. EP 1057812; JP 2000191641; WO 9942442 . |
| 【2】 Imamiya, E.; Fujiwara, S.; Watanabe, T.; Shiraishi, M.; Fukumoto, S.; Kusumoto, K.; Novel, non-acylguanidine type Na+/H+ exchanger inhibitors: Synthesis and biological evaluation of tetrahydroquinolinylidene aminoguanidine derivatives. 20th Symp Med Chem (Dec 6 2000, Tokyo) 2000, Abst 2P-02. |
| 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) | 48879 | 5-(5-fluoro-2-methylphenyl)-1,3-cyclohexanedione | C13H13FO2 | 详情 | 详情 | |
| (II) | 48880 | 3-amino-5-(5-fluoro-2-methylphenyl)-2-cyclohexen-1-one | C13H14FNO | 详情 | 详情 | |
| (III) | 48881 | Acetoacetaldehyde Dimethylacetal; 1,1-dimethoxy-3-butanone; 3-Ketobutyraldehyde dimethyl acetal; 3-Ketobutyric aAldehyde 1-dimethylacetal; 3-Oxobutyraldehyde dimethylacetal; 4,4-Dimethoxy-2-butanone | 5436-21-5 | C6H12O3 | 详情 | 详情 |
| (IV) | 48882 | 7-(5-fluoro-2-methylphenyl)-4-methyl-7,8-dihydro-5(6H)-quinolinone | C17H16FNO | 详情 | 详情 | |
| (V) | 10015 | 1-Hydrazinecarboximidamide; Hydrazinecarboximidamide | 79-17-4 | CH6N4 | 详情 | 详情 |