[5-Chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](2-fluorophenyl)methanone; 2-(2,2,2-Trifluoroethylamino)-5-chloro-2'-fluorobenzophenone -Drug Synthesis Database

【结构式】

【分子编号】33472

【品名】[5-Chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](2-fluorophenyl)methanone; 2-(2,2,2-Trifluoroethylamino)-5-chloro-2'-fluorobenzophenone

【CA登记号】

【分子式】C₁₅H₁₀ClF₄NO

【分子量】331.6968528

【元素组成】C 54.32% H 3.04% Cl 10.69% F 22.91% N 4.22% O 4.82%

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：(III)

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

Extended Information