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Styryl pyridine disulfide dinitrogen derivative and preparation method thereof

A technology of methylaminostyrene and tert-butoxycarbonylmethylaminostyrene, which is applied in the field of synthesis of radiopharmaceutical-labeled precursor compounds, and can solve problems such as no relevant reports

Inactive Publication Date: 2012-05-02
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no registration number on CA, and there are no related reports at home and abroad

Method used

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  • Styryl pyridine disulfide dinitrogen derivative and preparation method thereof
  • Styryl pyridine disulfide dinitrogen derivative and preparation method thereof

Examples

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Embodiment 1

[0033] Synthesis of tert-butyl 4-vinylphenylcarbamate (compound 1)

[0034] 4-Aminostyrene and di-tert-butylmethyl dicarbonate with 1.1 times the molar weight of 4-aminostyrene were dissolved in an appropriate amount of water, stirred at room temperature for 3 hours, a solid was formed, the solid was filtered out, dissolved in ethyl acetate, and the aqueous phase was washed with acetic acid Extract with ethyl ester, combine the organic phases, wash with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain light yellow solid compound 1, namely tert-butyl 4-vinylphenylcarbamate, which is directly used in Next reaction.

Embodiment 2

[0036] Synthesis of tert-butyl N-methyl-4-vinylphenylcarbamate (compound 2)

[0037] N 2 For protection, dissolve 6.7g (30mmol) of compound 1 in 30mL of anhydrous DMF, cool in an ice bath to about 0°C, slowly add 1.8g (45mmol) of 60% sodium hydride in 100mL of anhydrous DMF solution dropwise while stirring, and drop , raised to room temperature, 8.5g (60mmol) methyl iodide was slowly added dropwise to the reaction mixture, continued to stir for 2 hours, the reaction solution was carefully added to 200mL ice water, extracted with ethyl acetate (70mL×3 times), the ester layer Washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain red oil 2 (6.5 g, 89%), which was directly used in the next reaction.

Embodiment 3

[0039] Synthesis of 2-(2-(2-(5-iodopyridine-2-oxyl)ethoxy)ethoxy)ethanol (compound 3)

[0040] Dissolve 5g (17.6mmol) of 2-bromo-5-iodopyridine, 5.3g (70mmol) of triethylene glycol in 50mL of tetrahydrofuran, and add 2.35g (19mmol) of potassium tert-butoxide into the reaction solution in batches under stirring at room temperature. Reflux reaction for 24 hours, remove tetrahydrofuran under reduced pressure, add ethyl acetate and water, separate liquids, extract the aqueous phase with ethyl acetate, combine organic phases, wash with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate, remove under reduced pressure solvent to obtain a pale yellow oil, which solidified at room temperature and was separated by ethyl acetate column chromatography to obtain product 3 (2.34 g, 75%). [ 1 H] NMR (500MHz, CDCl 3 ) δ: 8.30 (1H, d), 7.76 (1H, d, d), 6.63 (1H, d), 4.44 (2H, t), 3.84 (2H, t), 3.73-3.60 (6H, m), 3.61 (2H,t).

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Abstract

The invention relates to a styryl pyridine disulfide dinitrogen derivative and a preparation method thereof and belongs to the field of a synthesis technology of a radiopharmaceutical labelled precursor compound. (E)-2-(2-(2-(2-(N-thiolethyl)-(N-(N-thiolethyl aminoethyl))aminoethoxy)ethoxy)ethoxy)-5-(4-methylaminostyryl) pyridine provided in the preparation method disclosed by the invention is called as BAT-AV-45 for short and is used for preparing a technetium-labelled radiopharmaceutical 99mTc-BAT-AV-45. The BAT-AV-45 has no a registration mark on the CA (Chemil Abstracts) and related reports of the BAT-AV-45 also do not exist at home and abroad. A medicine box can be conveniently prepared by mixing the BAT-AV-45 and other auxiliary materials and freezing and drying the mixture. The medicine box has high stability and over 95 percent of labelling yield and is convenient to be used for further researching biological characteristics. The technetium-labelled radiopharmaceutical 99mTc-BAT-AV-45 of the BAT-AV-45 is used for research work of SPECT (single photon emission computed tomography) development of an A alpha plaque.

Description

technical field [0001] The present invention relates to a kind of (E)-2-(2-(2-(2-(N-mercaptoethyl)-(N-(N-mercaptoethylaminoethyl))aminoethoxy)ethoxy The invention discloses a preparation method of )ethoxy)-5-(4-methylaminostyrene)pyridine, which belongs to the technical field of radiopharmaceutical labeling precursor compound synthesis. Background technique [0002] (E)-2-(2-(2-(2-(N-Mercaptoethyl)-(N-(N-Mercaptoethylaminoethyl))aminoethoxy)ethoxy)ethoxy) -5-(4-methylaminostyrene)pyridine (abbreviated as BAT-AV-45), its structural formula is shown in compound 7, and its molecular formula is C 26 h 40 N 4 o 3 S 2 , can conveniently form a stable complex with the isotope technetium 99m Tc-(E)-2-(2-(2-(2-(N-mercaptoethyl)-(N-(N-mercaptoethylaminoethyl))aminoethoxy)ethoxy)ethoxy base)-5-(4-methylaminostyrene)pyridine (referred to as 99m Tc-BAT-AV-45). [0003] With the gradual aging of the society, the number of patients with Alzheimer's disease (AD) is gradually increa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64C07F13/00A61K51/00A61K103/10
Inventor 张建康周杏琴钦晓峰
Owner JIANGSU INST OF NUCLEAR MEDICINE
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