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Positron emitted computerized tomography imaging agent benzamide derivative synthesizing method

A synthesis method and a formamide-based technology are used in the synthesis field of positron emission computed tomography imaging agent benzamide derivatives

Inactive Publication Date: 2004-09-15
JIANGSU INST OF NUCLEAR MEDICINE
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Problems solved by technology

Fallypride, the chemical name is (S)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5-fluoro[ 18 F] Propyl benzamide is a modification of the structure of epidepride, which is a positron nuclide with a short half-life 18 F labeling also maintains high affinity with D2 receptors and suitable lipophilicity. It is a new, safe and effective PET imaging agent for dopamine D2 receptors. There is no relevant report in China so far.

Method used

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  • Positron emitted computerized tomography imaging agent benzamide derivative synthesizing method

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Embodiment Construction

[0018] Preparation of (S)-(-)-2-carboxamido-N-(allyl)pyrrolidine (2):

[0019] Mix (S)-(-)-2-carboxamidopyrrolidine (0.12g, 1.0mmol) with 4ml of tetrahydrofuran, add sodium carbonate (0.05g, 0.5mmol), allyl bromide (0.12g, 1.0mmol ), reacted in an oil bath at 80°C for 24h. After the reaction, tetrahydrofuran was removed, and a small amount of water was added to the residue to adjust the pH to 10. Extracted with dichloromethane, combined organic layers, dried over anhydrous magnesium sulfate, filtered, concentrated to give white needle-like solid (2) (0.13g, 85%), mp 76~77°C (document [3] : 40%, 79-81°C).

[0020] Preparation of (S)-(-)-2-methylamino-N-(allyl)pyrrolidine (3):

[0021] (2) (0.16g, 1.04mmol) was dissolved by adding 2ml of tetrahydrofuran, cooled to -78°C in a low-temperature bath, added dropwise diisobutylaluminum hydride (0.89g, 6.23mmol), stirred for 30min, raised to room temperature, and continued to stir 48h. Add 1mol / L hydrochloric acid to terminate the...

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Abstract

The invention is a method to synthesize (S)-(-)-N-[(1-allyl-2-pyrrolidyl)methyl]-2,3-dimethoxy-5 -(3-hydroxy propyl)benzoic amide, relating to a technique to prepare PET developer. It adopts (S)-(-)-2-formamidopyrrol through allylation and electronation reaction to make (S)-(-)-2- methylamino-N-(allyl)pyrrol alkyl (3); adopts 2-hydroxy-3-methoxy methyl benzoate through allylation, Claisen rearrangement, hydroboration and hydrolyzation reaction to make 2,3-dimethoxy-5-(3-hydroxy propyl)benzoic acid (8); (3) and (8) react to make the aim compound. It improves the synthesis method reported in document, replacing expensive allyl iodide with allyl bromide to make the compound (3). It improves the purifying condition of intermediate.

Description

technical field [0001] A (S)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5-(3-hydroxypropyl)benzyl The synthesis method of amide, the compound is the fallypride label precursor, provides the basis for further preparation of brain receptor PET imaging agent, and relates to the preparation technology of PET imaging agent. Background technique [0002] Single photon emission computed tomography (SPECT) and positron emission computed tomography (PET) can be used to image brain receptors with high sensitivity and good resolution. Dopamine D2 receptor SPECT imaging agent 123 I / 131 I-epidepride (chemical name is (S)-(-)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5-iodo[ 123 I / 131 I] benzamide) has been successfully used to study the early diagnosis indicators of Parkinson's disease. Fallypride, the chemical name is (S)-(-)-N-[(1-allyl-2-pyrrolidinyl)methyl]-2,3-dimethoxy-5-fluoro[ 18 F] Propyl benzamide is a modification of the structure of epidepride, which ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/09
Inventor 杨敏项景德周杏琴曹国宪潘尚仁俞惠新张荣军
Owner JIANGSU INST OF NUCLEAR MEDICINE
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