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【结 构 式】 
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【分子编号】43739 【品名】4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide 【CA登记号】 |
【 分 子 式 】C13H20ClN3O2 【 分 子 量 】285.77352 【元素组成】C 54.64% H 7.05% Cl 12.41% N 14.7% O 11.2% |
合成路线1
该中间体在本合成路线中的序号：(II)The demethylation of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide (I) with EtS-Na in hot DMF gives the hydroxy compound (II), which is acylated with 3-chloro-2-butanone (III) by means of K2CO3 and NaI in DMF to yield 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(1-methyl-2-oxopropoxy)benzamide (IV). Finally, this compound is treated with HCl to furnish the target hydrochloride. Alternatively, the alkylation of the hydroxy compound (II) can also be performed by reaction of (II) with tetrabutylammonium bisulfate and NaOH to give the tetrabutylammonium phenolate (V), which is alkylated with the chlorobutanone (III) to give (IV).
| 【1】 Monkovic, I.; NEW BENZAMIDE ANTI-EMETICS. Drugs Fut 1989, 14, 1, 41. |
| 【2】 Monkovic, I.; Willner, D.; Adam, M.A.; Brown, M.; Crenshaw, R.R.; Fuller, C.E.; Juby, P.F.; Luke, G.M.; Matiskella, J.A.; Montzka, T.A.; Substituted benzamides. 1. Potential nondopaminergic antagonists of chemotherapy-induced nausea and emesis. J Med Chem 1988, 31, 8, 1548-58. |
| 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) | 12421 | 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide | 364-62-5 | C14H22ClN3O2 | 详情 | 详情 |
| (II) | 43739 | 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide | C13H20ClN3O2 | 详情 | 详情 | |
| (III) | 12423 | 3-Chloro-2-butanone | 4091-39-8 | C4H7ClO | 详情 | 详情 |
| (IV) | 12424 | 4-Amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(1-methyl-2-oxopropoxy)benzamide | C17H26ClN3O3 | 详情 | 详情 | |
| (V) | 43740 | N,N,N-tributyl-1-butanaminium 5-amino-4-chloro-2-([[2-(diethylamino)ethyl]amino]carbonyl)benzenolate | C29H55ClN4O2 | 详情 | 详情 |