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Tetrahydroisoquinoline derivative and synthesis method thereof

A technology of tetrahydroisoquinoline and its derivatives, applied in organic chemistry and other fields

Inactive Publication Date: 2014-05-14
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The compounds involved in the present invention are a class of tetrahydroisoquinoline derivatives with novel side chain structures, and these compounds have not been reported in other patent documents at present

Method used

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  • Tetrahydroisoquinoline derivative and synthesis method thereof
  • Tetrahydroisoquinoline derivative and synthesis method thereof
  • Tetrahydroisoquinoline derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of 1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

[0027] Add 100 g of 2-benzyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid into 2L of methanol, then add 10 g of 10% Pd / C, pass in hydrogen, stir the reaction at room temperature for 24 hours, stop React, filter, and concentrate the filtrate under reduced pressure to obtain 1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid.

[0028] (2) Synthesis of 2-(4-(ethoxycarbonyl)-5-iodothiazol-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid

[0029] Add 60g of 1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid, 90g of ethyl 2-chloro-5-iodothiazole-4-carboxylate, and 55g of anhydrous potassium carbonate to 800ml N,N- In dimethylformamide, heat to reflux, stir for 10 hours, stop the reaction, remove most of N,N-dimethylformamide under reduced pressure, extract the residue with ethyl acetate and water, and collect the organic phase. After drying, concentration and separation on a silica gel column, 136.8 g o...

Embodiment 2

[0036] Synthesis of ethyl-5-iodo-2-(8-(p-methylphenylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid ethyl ester

[0037] Add 35g of p-methylaniline to 800ml of ethyl acetate, then add 50ml of pyridine, cool down to 0°C, and dropwise add 125g of ethyl 2-(8-(chlorocarbonyl)-3,4-dihydroisoquinoline-2 (1H)-yl)-5-iodothiazole-4-carboxylic acid ethyl ester, keep the temperature of the system not exceeding 10°C, after the dropwise addition, continue to stir at 0°C for 14 hours, slowly pour the reaction solution into ice water, add dilute hydrochloric acid, stirred, separated, collected the organic phase, dried, concentrated and separated on a silica gel column to obtain 129.8g of ethyl-5-iodo-2-(8-(p-methylphenylcarbamoyl)-3,4-di Hydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid ethyl ester.

[0038] H1-NMR (CDCl 3 ,400M):8.72(1H,brs),7.76~7.65(3H,m),7.34~7.26(4H,m),7.17(1H,m),4.26~4.12(4H,m),3.42(2H,t ), 2.66(2H,t), 2.31(3H,s), 1.31(3H,t).

Embodiment 3

[0040] Ethyl-5-iodo-2-(8-(m-methoxyphenylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylic acid ethyl ester synthesis

[0041]Add 40g of m-methoxyaniline to 800ml of ethyl acetate, then add 50ml of pyridine, cool down to 0°C, and dropwise add 125g of ethyl 2-(8-(chlorocarbonyl)-3,4-dihydroisoquinoline- 2(1H)-yl)-5-iodothiazole-4-carboxylic acid ethyl ester, keep the temperature of the system not exceeding 10°C, after the dropwise addition, continue to stir at 0°C for 14 hours, slowly pour the reaction solution into ice water, add dilute hydrochloric acid, stirred, separated, collected the organic phase, dried, concentrated and separated on a silica gel column to obtain 132.3g of ethyl-5-iodo-2-(8-(p-methylphenylcarbamoyl)-3,4- Ethyl dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate.

[0042] H1-NMR (CDCl 3 ,400M):8.73(1H,brs),7.79~7.67(5H,m),7.35~7.26(2H,m),7.15(1H,m),4.23~4.11(4H,m),3.78(3H,s ), 3.46(2H,t), 2.67(2H,t), 1.32(3H,t).

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Abstract

The invention discloses a tetrahydroisoquinoline derivative and a synthesis method thereof. The name of the compound is ethyl-5-iodine-2-(8-(substituted phenyl amino formoxyl)-3,4-dihydrogen isoquinoline-2 (1H)-yl) thiazole-4-Nonanoic acid-ethyl ester. The target product is obtained from 2-benzyl-1,2,3,4-tetrahydroisoquinoline-8-carboxylic acid as an initial raw material by debenzylation, substitution, acylation and condensation. The compound has potential biological activity.

Description

technical field [0001] The present invention relates to a novel preparation method of tetrahydroisoquinoline derivatives, in particular to the compound ethyl-5-iodo-2-(8-(substituted phenylcarbamoyl)-3,4-dihydroisoquinoline-2 A preparation method of (1H)-yl)-4,5-dihydrothiazole-4-carboxylic acid ethyl ester. technical background [0002] Compound ethyl-5-iodo-2–(8-(substituted phenylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-4,5-dihydrothiazol-4- Ethyl carboxylate, the structural formula is: [0003] [0004] Tetrahydroisoquinoline derivatives with complex and variable structures are important components of modern medicines and the source of new drug development. They have a wide range of biological activities such as antihypertensive, antifungal, antiarrhythmic, antiviral, antibacterial and strong antioxidant activity. The history of the discovery of tetrahydroisoquinoline derivatives is not very long. In 1974, Canadian scientist Kluepfel et al. isolated the first ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04
CPCC07D417/04
Inventor 陈芳军邓泽平
Owner 湖南华腾制药有限公司
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