N-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenyl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】28311

【品名】N-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenyl]acetamide

【CA登记号】

【分子式】C₂₂H₁₈ClNO

【分子量】347.84376

【元素组成】C 75.97% H 5.22% Cl 10.19% N 4.03% O 4.6%

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 reaction of 4-aminobenzophenone (I) with benzylmagnesium bromide (II) in ether gives the carbinol (III), which by reaction with acetic anhydride in hot pyridine yields the olefinic acetamide (IV). The chlorination of (IV) with Cl2 in CCl4 followed by refluxing in the same solvent affords the chlorovinyl acetamide (V), which is alkylated at the amidic nitrogen with 2-chloroethyl(diethyl)amine (VI) by means of KOH in refluxing acetone giving the disubstituted acetamide (VII). Finally, the deacetylation of (VII) with hot 10% HCl and salification with citric acid affords the target compound.

参考文献中间体

合成目标

【1】 Bitonti, A.J.; Baumann, R.J. (Merrell Pharmaceuticals, Inc.); Non-metabolizable clomiphene analogs for treatment of tamoxifen-resistant tumors. EP 0660821; JP 1997500863; WO 9406762 .

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)	28307	(4-aminophenyl)(phenyl)methanone	1137-41-3	C₁₃H₁₁NO	详情	详情
(II)	28308	benzyl(bromo)magnesium; benzylmagnesium bromide	1589-82-8	C₇H₇BrMg	详情	详情
(III)	28309	1-(4-aminophenyl)-1,2-diphenyl-1-ethanol		C₂₀H₁₉NO	详情	详情
(IV)	28310	N-[4-[(Z)-1,2-diphenylethenyl]phenyl]acetamide		C₂₂H₁₉NO	详情	详情
(V)	28311	N-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenyl]acetamide		C₂₂H₁₈ClNO	详情	详情
(VI)	16194	2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine	100-35-6	C₆H₁₄ClN	详情	详情
(VII)	28312	N-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenyl]-N-[2-(diethylamino)ethyl]acetamide		C₂₈H₃₁ClN₂O	详情	详情

Extended Information