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Improvement of 5-tri-n-butyl tin-2-[2-(dimethylamino methylbenzenethio)] aniline

A technology of dimethylaminomethyl phenyl and synthesis method, which is applied in the synthesis field of iodine-labeled precursor and achieves the effect of stable properties

Inactive Publication Date: 2005-02-23
JIANGSU INST OF NUCLEAR MEDICINE
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Problems solved by technology

[0004] For the existing relevant synthetic routes, see literature [1] Yiyun Huang, et al, Nuclear Medicine and Biology, Vol.29, pp.741~751. Reports, only seen for the synthesis of 5-bromo-2-[2-(dimethyl Aminomethylphenylmercapto)]benzylamine

Method used

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  • Improvement of 5-tri-n-butyl tin-2-[2-(dimethylamino methylbenzenethio)] aniline
  • Improvement of 5-tri-n-butyl tin-2-[2-(dimethylamino methylbenzenethio)] aniline
  • Improvement of 5-tri-n-butyl tin-2-[2-(dimethylamino methylbenzenethio)] aniline

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Embodiment Construction

[0016] Synthesis of 2-(4-bromo-2-nitrophenylmercapto)benzoic acid (product 3)

[0017] Take 2,5-dibromonitrobenzene (11.8g, 42mmoL), 2-mercaptobenzoic acid (6.2g, 40mmoL), copper powder (0.73g) and potassium carbonate (12.7g) and add 100mL N, N-dimethyl Dimethyl formamide (DMF), heated to 65°C, and the reaction was stirred overnight. The reaction solution was cooled to room temperature, poured into ice water, filtered, the filtrate was acidified with 6N HCl, extracted three times with dichloromethane, the organic layers were combined, washed with water, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation to obtain a crude product, which was recrystallized from ethanol to obtain product 3 (14g), yellow solid, mp 162~164 ℃, productive rate is 94%, IR (cm -1 ): 3083,1680,1532,1344; MS: 354,352(M-1) (because product 3 contains bromine, two isotope peaks of bromine are reflected in the mass spectrum); NMR: δ8.26(d, 1H ), 8.06-8.12 (dd, 1H), 7.42-7.58 (m, 4...

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Abstract

Synthesis of 5 - tri- n - butylstannum -2 - [2- (dimethyl aminemethylbenzensulfhydryl anilin is improved. It refers to synthesis of iodine labeled prosome. SnBu3 - ADAM is * I - ADAM' labeled prosome which has appetence and selectivity with 5- hydroxytryptamine translocator. It provides the diagnosis evidence for depression through studying distribution of * I - ADAM in brain to get distribution image brain internal. This invention provides an improved SnBu3 - ADAM synthesis route with 2,5-dibromonitobenzen and 2-sulfhydryl benzoic acid as start materials, of which both are cheap, has stable property. It yields higher than reports in literature.

Description

technical field [0001] An improvement to the synthesis method of 5-tri-n-butyltin-2-[2-(dimethylaminomethylphenylmercapto)]aniline involves the synthesis of iodine-labeled precursors. Background technique [0002] At present, it is generally believed that 5-hydroxytryptamine (5-HT) plays an important role in regulating the functions of the central nervous system in the brain, such as regulating mood, appetite, sleep, pain and aggressive behavior, and is also closely related to depression. The serotonin transporter (SERT), located in the middle and terminal of serotonin neurons, regulates the level of serotonin. Many antidepressant drugs reduce the reabsorption of serotonin by binding to the 5-HT transporter, thus playing an antidepressant role. [0003] 5-tri-n-butyltin-2-[2-(dimethylaminomethylphenylmercapto)]aniline, [5-(tri-n-butyltin)-2-((2-((dimethylamino)methyl)phenyl) thio)phenylamine], abbreviated as SnBu 3 -ADAM, is *I-ADAM[2-((2-((dimethylamino)methyl)phenyl)thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/22
Inventor 陆春雄吴春英蒋泉福陈正平傅榕赓张同兴李晓敏王颂佩朱钧清曹国宪项景德
Owner JIANGSU INST OF NUCLEAR MEDICINE
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