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

【结构式】

【分子编号】28312

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

【CA登记号】

【分子式】C₂₈H₃₁ClN₂O

【分子量】447.01972

【元素组成】C 75.23% H 6.99% Cl 7.93% N 6.27% O 3.58%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

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

合成路线2

该中间体在本合成路线中的序号：(VI)

The acetylation of 4-aminobenzophenone (I) with acetic anhydride and TEA in dichloromethane gives the acetamide (II), which is N-alkylated with 2-chlorethyl(diethyl)amine (III) by means of KOH in refluxing acetone yielding the disubstituted acetamide (IV). The reaction of the ketonic group of (IV) with benzylphosphonic acid diethyl ester (V) by means of butyllithium and benzenesulfonyl chloride in THF affords the chlorovinyl acetamide (VI), which is finally hydrolyzed with HCl and salified with citric acid to provide the target compound.

参考文献中间体

合成目标

【1】 Bitonti, A.J. (Aventis Pharmaceuticals, Inc.); Method of using triaryl-ethylene derivs. in the treatment and prevention of osteoporosis. US 5691384; WO 9616646 .

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)	28313	N-(4-benzoylphenyl)acetamide		C₁₅H₁₃NO₂	详情	详情
(III)	16194	2-chloro-N,N-diethyl-1-ethanamine; N-(2-chloroethyl)-N,N-diethylamine	100-35-6	C₆H₁₄ClN	详情	详情
(IV)	28314	N-(4-benzoylphenyl)-N-[2-(diethylamino)ethyl]acetamide		C₂₁H₂₆N₂O₂	详情	详情
(V)	28315	diethyl benzylphosphonate	1080-32-6	C₁₁H₁₇O₃P	详情	详情
(VI)	28312	N-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenyl]-N-[2-(diethylamino)ethyl]acetamide		C₂₈H₃₁ClN₂O	详情	详情

Extended Information