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Synthesis of PET imaging agent prosome isoquinoline methanamide derivant

A technology of PET imaging agent and isoquinoline formamide, which is applied in the new synthesis of 1-isoquinoline-3-carboxamide compounds and the synthesis field of isoquinoline formamide derivatives of PET imaging agent marking precursors , can solve the problems of low yield of PET imaging agent labeling precursor, cumbersome steps, complicated operation, etc., and achieve the effect of simplifying industrial production equipment and production process, simple process and high product purity

Inactive Publication Date: 2009-05-13
CHANGSHU INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The main purpose of the present invention is to provide a kind of synthetic method of PET imaging agent precursor isoquinoline carboxamide derivative, and this method has solved the PET imaging agent marking precursor production rate that ubiquitous in the prior art is not high, cost More expensive; and the steps are cumbersome and complicated to operate

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  • Synthesis of PET imaging agent prosome isoquinoline methanamide derivant
  • Synthesis of PET imaging agent prosome isoquinoline methanamide derivant
  • Synthesis of PET imaging agent prosome isoquinoline methanamide derivant

Examples

Experimental program
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Effect test

Embodiment 1

[0067] Preparation of 1-(2-chlorophenyl)-N-isobutylisoquinoline-3-carboxamide

[0068] Preparation of 2-chlorohippuric acid:

[0069] Place 250ml of 3% sodium hydroxide solution in an ice bath for cooling, add 15g of glycine and stir to dissolve, then slowly drop a mixed solution of 25ml of o-chlorobenzoyl chloride and 100ml of toluene. After the dropwise addition was completed, the reaction was continued at room temperature for 3 hours. After the reaction is complete, adjust the pH to 2-3 with dilute hydrochloric acid. Stand still, filter with suction, and dry to obtain white crystals. The white crystals were dried and weighed. 34.1 g of white crystals were obtained with a yield of 79.8%.

[0070] IRv(KBr) / cm -1 : 3286, 1724, 1628;

[0071] 1 H-NMR: 4.18 (d, 2H, J = 5.8 Hz), 7.39-7.85 (m, 5H).

[0072] Preparation of 4-benzylidene-2-(2-chlorophenyl)oxazol-5-one:

[0073] Add 5.340g of 2-chlorohippuric acid, 2.660g of benzaldehyde, 3.190g of sodium acetate and 75ml of...

Embodiment 2

[0089] Preparation of 1-(2-chlorophenyl)-N-tert-butylisoquinoline-3-carboxamide

[0090] Preparation of 2-chlorohippuric acid:

[0091] Place 250ml of 15% sodium hydroxide solution in an ice bath for cooling, add 15g of glycine and stir to dissolve, then slowly drop a mixed solution of 15ml of o-chlorobenzoyl chloride and 100ml of toluene. After the dropwise addition was completed, the reaction was continued at room temperature for 2 hours. After the reaction is complete, adjust the pH to 3 with dilute hydrochloric acid. Stand still, filter with suction, and dry to obtain white crystals. The white crystals were dried and weighed. 35.2 g of white crystals were obtained with a yield of 81.3%.

[0092] IRv(KBr) / cm -1 : 3286, 1724, 1628;

[0093] 1 H-NMR: 4.18 (d, 2H, J = 5.8 Hz), 7.39-7.85 (m, 5H).

[0094] Preparation of 4-benzylidene-2-(2-chlorophenyl)oxazol-5-one:

[0095] Add 5.340g of 2-chlorohippuric acid, 3.320g of benzaldehyde, 3.190g of sodium acetate and 75ml of ...

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Abstract

The invention discloses a synthetic method for an isoquinoline formamide derivative of PET developer precursor, and belongs to the field of synthesis of stable isotope labeled precursor. The method is as follows: a) glycin and o-chlorobenzoyl chloride with proper molar ratio are subjected to acylation reaction under alkaline environment to obtain 2-chloro hippuric acid; b) the 2-chloro hippuric acid obtained in step a) and benzaldehyde are subjected to cyclization reaction under appropriate temperature, and proper amount of catalyst is added into the mixture for molecule rearrangement to obtain 1-(2-chlorpheyl)isoquinoline-3-methanoic acid; and c) the 1-(2-chlorpheyl) isoquinoline-3-methanoic acid reacts with halogeno reagent and then is ammonolyzed to obtain a compound as general formula (I). The synthetic method has the advantages that the synthetic method shortens synthetic route, reduces synthetic cost, is simple, convenient and practical, and has higher yield.

Description

technical field [0001] The invention belongs to the synthetic field of stable isotope labeling precursors, in particular to a preparation method of a PET imaging agent labeling precursor, specifically a synthetic method of a PET imaging agent labeling precursor isoquinoline formamide derivative, namely A new method for the synthesis of 1-(2-chlorophenyl)isoquinoline-3-carboxamides. Background technique [0002] Positron Emission Computed Tomography (PET, Positron Emission Computed Tomography) is a very small amount of short-lived positron reflective nuclides such as labeled precursor compounds 11 C. 18 F is made into an imaging agent and injected into the human body, and then a special detection device is used to detect the distribution of these positron markers in the body; due to the different metabolic states of different tissues, the distribution of these nuclide-labeled substances in various tissues of the human body The distribution is also different. For example, it...

Claims

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Application Information

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IPC IPC(8): C07D217/26A61K51/04A61K101/00
Inventor 柴文袁荣鑫程洪见殷文宇石磊徐志红桂媛钱桅
Owner CHANGSHU INSTITUTE OF TECHNOLOGY
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