2-Amino-5-chloro-2'-fluorobenzophenone; (2-Amino-5-chlorophenyl)(2-fluorophenyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】32281

【品名】2-Amino-5-chloro-2'-fluorobenzophenone; (2-Amino-5-chlorophenyl)(2-fluorophenyl)methanone

【CA登记号】784-38-3

【分子式】C₁₃H₉ClFNO

【分子量】249.6717032

【元素组成】C 62.54% H 3.63% Cl 14.2% F 7.61% N 5.61% O 6.41%

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：(II)

The alkylation of 2-amino-5-chloro-2'-fluorobenzophenone (II) with 2,2,2-trifluoroethyl trichloromethylsulfonate (A) gives 2-(2,2,2-trifluoroethylamino)-5-chloro-2'-fluorobenzophenone (III), which is bromoacetylated with bromoacetyl chloride (B) in refluxing benzene yielding the bromoacetanilide (IV).This compound is cyclized with NH3 in chloroform affording 7-chloro-1-(2,2,2-trifluoroethyl)-1,3-dihydro-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one (I), which by reaction with P2S5 in refluxing dioxane gives the target compound.

参考文献中间体

合成目标

【1】 Steinman, M.; Benzodiazepines and the process for their manufacture. DE 2138773; ES 393953; FR 2102114; GB 1345938 .
【2】 Steinman, M.; 1-Polyfluoroalkyl-1,4-benzodiazepin-2-thiones for effecting tranquilization, sedation and treating colvulsions. US 3920818 .
【3】 Castaner, J.; Thorpe, P.; Quazepam. Drugs Fut 1978, 3, 2, 139.
【4】 Topliss, J.G.; Steinman, M.; Alekel, R.; Wong, Y.S.; York, E.E.; 1-Polyfluoroalkylbenzodiazepines. J Med Chem 1973, 16, 12, 1354-60.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	27903	2-Bromoacetyl chloride	22118-09-8	C₂H₂BrClO	详情	详情
(A)	33474	2,2,2-Trifluoroethyl trichloromethanesulfonate; 2,2,2-Trifluoroethyl trichloromethylsulfonate	23199-56-6	C₃H₂Cl₃F₃O₃S	详情	详情
(I)	33471	7-Chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one		C₁₇H₁₁ClF₄N₂O	详情	详情
(II)	32281	2-Amino-5-chloro-2'-fluorobenzophenone; (2-Amino-5-chlorophenyl)(2-fluorophenyl)methanone	784-38-3	C₁₃H₉ClFNO	详情	详情
(III)	33472	[5-Chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](2-fluorophenyl)methanone; 2-(2,2,2-Trifluoroethylamino)-5-chloro-2'-fluorobenzophenone		C₁₅H₁₀ClF₄NO	详情	详情
(IV)	33473	2-bromo-N-[4-chloro-2-(2-fluorobenzoyl)phenyl]-N-(2,2,2-trifluoroethyl)acetamide		C₁₇H₁₁BrClF₄NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

2-Amino-5-chloro-2'-fluorobenzophenone (I) is condensed with monoethyl methoxycarbonyl aminomalonate (II) and the crude product obtained (III) is deprotected by HBr to give the free amine hydrobromide (IV). This product is then cyclized in a mixture of acetic acid-sodium acetate to obtain CM-6912, which is separated by filtration and recrystallized in ethanol.

参考文献中间体

合成目标

【1】 Demarne, H.; Hallot, A.; Benzodiazepine derivatives and pharmaceutical compositions thereof. DE 2719608; FR 2350346; GB 1538164; JP 57081472; NL 7704911; NL 7704912; US 4235897 .
【2】 Dubois, M.; Ethyl Loflazepate. Drugs Fut 1981, 6, 12, 772.

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)	32281	2-Amino-5-chloro-2'-fluorobenzophenone; (2-Amino-5-chlorophenyl)(2-fluorophenyl)methanone	784-38-3	C₁₃H₉ClFNO	详情	详情
(II)	32282	3-ethoxy-N-(methoxycarbonyl)-3-oxoalanine		C₇H₁₁NO₆	详情	详情
(III)	32283	ethyl 3-[4-chloro-2-(2-fluorobenzoyl)anilino]-2-[(methoxycarbonyl)amino]-3-oxopropanoate		C₂₀H₁₈ClFN₂O₆	详情	详情
(IV)	32284	ethyl 2-amino-3-[4-chloro-2-(2-fluorobenzoyl)anilino]-3-oxopropanoate		C₁₈H₁₆ClFN₂O₄	详情	详情

Extended Information