[5-chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](phenyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】33848

【品名】[5-chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](phenyl)methanone

【CA登记号】

【分子式】C₁₅H₁₁ClF₃NO

【分子量】313.7063896

【元素组成】C 57.43% H 3.53% Cl 11.3% F 18.17% N 4.46% O 5.1%

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：(III)

1) The alkylation of 2-amino-5-chlorobenzophenone (I) with 2,2,2-trifluoroethyl trichloromethansulfonate (II) in refluxing xylene gives the N-trifluoroethyl derivative (III), which is then cyclized with glycine ethyl ester (A) in refluxing pyridine. 2) Compound (III) can also be bromoacetylated with bromoacetyl bromide (B) in refluxing benzene yielding the N-bromoacetyl compound (IV), which is then cyclized with ammonia in CHCl3. 3) By alkylation of 7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IX) with NaOMe and 2,2,2-trifluoroethyl iodide in MeOH.

参考文献中间体

合成目标

【1】 Topliss, J.G.; 2-Polyfluoroweralkyl benzophenones. US 3641147 .
【2】 Topliss, J.G.; 1-Polyhalogenoalkyl-2-oxo-1,3-dihydro-2H-14-benzodiazepines. US 3429874 .
【3】 Topliss, J.G.; Verfahren zur Herstellung von neuen 1,4-benzodiazepinen bzw. ihren 4-Oxyden. CH 505842; DE 1793682; FR 1518382; GB 1179125 .
【4】 Castaner, J.; Thorpe, P.; Halazepam. Drugs Fut 1978, 3, 2, 109.
【5】 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
	18806	1,1,1-trifluoro-2-iodoethane	353-83-3	C₂H₂F₃I	详情	详情
(A)	10309	ethyl 2-aminoacetate; Glycine ethyl ester	459-73-4	C₄H₉NO₂	详情	详情
(B)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(I)	10279	(2-Amino-5-chlorophenyl)(phenyl)methanone; 2-Amino-5-chlorobenzophenone	719-59-5	C₁₃H₁₀ClNO	详情	详情
(II)	33474	2,2,2-Trifluoroethyl trichloromethanesulfonate; 2,2,2-Trifluoroethyl trichloromethylsulfonate	23199-56-6	C₃H₂Cl₃F₃O₃S	详情	详情
(III)	33848	[5-chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](phenyl)methanone		C₁₅H₁₁ClF₃NO	详情	详情
(IV)	33849	N-(2-benzoyl-4-chlorophenyl)-2-bromo-N-(2,2,2-trifluoroethyl)acetamide		C₁₇H₁₂BrClF₃NO₂	详情	详情
(IX)	10281	7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 1,4-benzdiazepin-2-one-5-phenyl-7-chloro	1088-11-5	C₁₅H₁₁ClN₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

N-trifluoroethyl derivative (III) can also be obtained by alkylation of (X) with (II) in refluxing xylene giving 4-chloro-N-(2,2,2-trifluoroethyl)aniline (XV), followed by a Friedel-Crafts reaction with benzoyl chloride by means of AlCl3.

参考文献中间体

合成目标

【1】 Topliss, J.G.; 1-Polyhalogenoalkyl-2-oxo-1,3-dihydro-2H-14-benzodiazepines. US 3429874 .
【2】 Topliss, J.G.; 2-Polyfluoroweralkyl benzophenones. US 3641147 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	33474	2,2,2-Trifluoroethyl trichloromethanesulfonate; 2,2,2-Trifluoroethyl trichloromethylsulfonate	23199-56-6	C₃H₂Cl₃F₃O₃S	详情	详情
(III)	33848	[5-chloro-2-[(2,2,2-trifluoroethyl)amino]phenyl](phenyl)methanone		C₁₅H₁₁ClF₃NO	详情	详情
(X)	12034	4-Chlorophenylamine; 4-Chloroaniline; p-Chloroaniline	106-47-8	C₆H₆ClN	详情	详情
(XV)	33475	N-(4-chlorophenyl)-N-(2,2,2-trifluoroethyl)amine; 4-chloro-N-(2,2,2-trifluoroethyl)aniline		C₈H₇ClF₃N	详情	详情

Extended Information