2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】27480

【品名】2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone

【CA登记号】

【分子式】C₁₂H₁₁BrCl₂O

【分子量】322.02814

【元素组成】C 44.76% H 3.44% Br 24.81% Cl 22.02% O 4.97%

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)

Addition of methylmagnesium iodide to nitrile (I), followed by hydrolytic treatment, provided ketone (II), which was brominated in CHCl3-MeOH to give bromomethyl ketone (III). Alkylation of thiourea (V) with 3-(dimethylamino)propyl chloride (IV) produced S-alkyl isothiourea (VI). After hydrolysis of (VI) with NaOEt, the intermediate thiol (VII) was condensed with bromoketone (III) to yield the required thioether, which was finally converted to the citrate salt.

参考文献中间体

合成目标

【1】 Harris, P.J.; Heal, D.J. (The Boots Company plc); 1-Arylcycloalkyl sulphides, sulphoxides and sulphones for the treatment of depression, anxiety and Parkinson's disease. EP 0715620; JP 1996510222; US 5652271; WO 9426704 .

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)	27478	1-(3,4-dichlorophenyl)cyclobutanecarbonitrile		C₁₁H₉Cl₂N	详情	详情
(II)	27479	1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone		C₁₂H₁₂Cl₂O	详情	详情
(III)	27480	2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-1-ethanone		C₁₂H₁₁BrCl₂O	详情	详情
(IV)	24581	3-(Dimethylamino)propyl chloride; 3-Chloro-N,N-dimethyl-1-propanamine	5407-04-5	C₅H₁₂ClN	详情	详情
(V)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(VI)	27481	1-[[amino(imino)methyl]sulfanyl]-3-(dimethylamino)propane		C₆H₁₅N₃S	详情	详情
(VII)	27482	N,N-Dimethyl-N-(3-sulfanylpropyl)amine sodium salt		C₅H₁₂NNaS	详情	详情

Extended Information