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【结 构 式】

【分子编号】43740

【品名】N,N,N-tributyl-1-butanaminium 5-amino-4-chloro-2-([[2-(diethylamino)ethyl]amino]carbonyl)benzenolate

【CA登记号】

【 分 子 式 】C29H55ClN4O2

【 分 子 量 】527.23416

【元素组成】C 66.07% H 10.51% Cl 6.72% N 10.63% O 6.07%

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:(V)

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
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