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A technology of iopromide and a new method, which is applied in the field of preparation of iopromide, can solve the problems of reducing the polarity of compounds, expensive raw materials are not easy to obtain, double-substituted by-products are not easy to remove, etc., and achieve the effect of high yield
Inactive Publication Date: 2015-10-28
SHENYANG J & HEALTH PHARMA
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[0025] Method 6 reduces the polarity of the compound through the protection of the methoxyacetyl group, and then removes the double-substituted by-products by crystallization. Although this method reduces the reaction steps, there are more expensive starting materials, larger protecting groups, and difficult Disadvantages such as deprotection
[0026] In summary, the current synthesis process has disadvantages such as difficult removal of double-substituted by-products, many reaction steps, introduction of protective groups, and expensive and difficult-to-obtain raw materials. The introduction of protective groups, cheap and easy-to-obtain raw materials, and high-yield, high-purity preparation of iopromide are of great significance
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Embodiment 1
[0041] Example 1: Synthesis of 5-amino-3-allylcarbamoyl-2,4,6-triiodobenzoyl chloride (formula III):
[0042] Method 1: Dissolve 5-amino-2,4,6-triiodoisophthalic acid dichloride (Formula II) (100.0g, 0.17mol) in 500mlTHF, cool down in an ice-salt bath to below 0°C, add dropwise 500ml of allylamine (30.5g, 0.53mol) solution dissolved in THF was added after dropping, and reacted below 0°C for 10h. After the reaction was completed, suction filtered, and the filtrate was evaporated to dryness to obtain a light yellow white powder. The crude product was slurried with dichloromethane, filtered with suction, and the filtrate was evaporated to dryness to obtain 62.1 g of beige powder with a molar yield of 60%.
[0043] Method 2: N,N-dimethylformamide was used as the reaction solvent, allylamine (10.96g, 0.19mol) was operated as above, and the reaction was carried out at room temperature for 8 hours, and the product yield was 61%.
[0044] Method 2: Using N,N-dimethylformamide as the ...
Embodiment 2
[0045] Example 2: Synthesis of 5-methoxyacetamido-2,4,6-triiodoisophthaloyl chloride (Formula III-1):
[0046] Dissolve methoxyacetyl chloride (54.6g, 0.50mol) in 100mL of dry DMA, add dropwise 5-amino-2,4,6-triiodoisophthalic acid dichloride (Formula II) at 10°C (100.0 g, 0.17 mol) of DMA solution in 300 mL, after dropping, react at room temperature for 24 hours. After the reaction is completed, the reaction solution is poured into ice water, and a white solid is precipitated immediately, stirred for 15 min, filtered with suction, and the filter cake is dissolved in dichloromethane, and then washed with saturated NaHCO 3 solution and saturated NaCl solution were washed twice, and the organic layer was placed in the refrigerator with a small amount of anhydrous NaCl 2 SO 4 After drying overnight and removing the solvent, 101.1 g of a white solid was obtained, and the molar yield was 90.2%.
[0047] Example: 3: Synthesis of 5-amino-N-methyl-N, N'-diallyl-2,4,6-triiodoisophth...
Embodiment 4
[0051] Example 4: Preparation of 5-methoxyacetamido-3-allylcarbamoyl-2,4,6-triiodobenzoyl chloride (Formula IV-1):
[0052] Method 1: At room temperature, dissolve methoxyacetyl chloride (31.7g, 0.29mol) in 300mlTHF, and add it dropwise to 5-amino-3-allylcarbamoyl-2,4,6-triiodobenzene Formyl chloride (formula III) (60.0 g, 0.10 mol) in 300 ml THF was added dropwise and reacted at room temperature. After the reaction, evaporate to dryness under reduced pressure to obtain 65.0 g of white powder with a molar yield of 97%.
[0053] Method 2: Using N,N-dimethylformamide as the reaction solvent, the operation is the same as above, and the product yield is 95%.
[0054] Method 2: Using N,N-dimethylformamide as the reaction solvent, the operation is the same as above, and the product yield is 97%.
[0055] Method 4: Use acetonitrile as the reaction solvent, add triethylamine (29.0 g, 0.29 mol), after the reaction is completed, filter with suction, and evaporate the reaction liquid to ...
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Abstract
The present invention relates to iopromide preparation methods, and provides three new iopromide preparation methods, wherein the method 1 comprises that a compound represented by a formula II is adopted as a starting raw material and reacts with allylamine to obtain a compound represented by a formula III, the compound represented by the formula III reacts with N-methyl allylamine to obtain a compound represented by a formula IV, the compound represented by the formula IV reacts with methoxyacetyl chloride to obtain a compound represented by a formula V, and the compound represented by the formula V is oxidized to obtain the iopromide represented by a formula I, the method 2 comprises that the compound represented by the formula II is adopted as a starting raw material and reacts with allylamine to obtain the compound represented by the formula III, the compound represented by the formula III reacts with methoxyacetyl chloride to obtain a compound represented by a formula IV-1, the compound represented by the formula IV-1 reacts with N-methyl allylamine to obtain the compound represented by the formula V, and the compound represented by the formula V is oxidized to obtain the iopromide represented by the formula I, the method 3 comprises that the compound represented by the formula II is adopted as a starting raw material and reacts with allylamine to obtain the compound represented by the formula III, the compound represented by the formula III reacts with methoxyacetyl chloride to obtain the compound represented by the formula IV-1, the compound represented by the formula IV-1 reacts with 3-methylamino-1,2-propanediol to obtain a compound represented by a formula V-1, and the compound represented by the formula V-1 is oxidized to obtain the iopromide represented by the formula I, and the method 4 comprises that the compound represented by the formula II is adopted as a starting raw material and reacts with methoxyacetyl chloride obtain a compound represented by a formula III-1, the compound represented by the formula III-1 reacts with allylamine to obtain the compound represented by the formula IV-1, the compound represented by the formula IV-1 reacts with N-methyl allylamine to obtain the compound represented by the formula V, and the compound represented by the formula V is oxidized to obtain the iopromide represented by the formula I.
Description
Technical field: [0001] The present invention relates to a preparation method of iopromide, and provides three new methods for preparing iopromide: method 1: using formula II as a starting material, reacting with allylamine to obtain formula III, and reacting formula III with N-methylallylamine Formula IV is obtained, formula IV is reacted with methoxyacetyl chloride to obtain formula V, and formula V is oxidized to obtain iopromide formula I; method 2: using formula II as the starting material, reacting with allylamine to obtain formula III, formula III and Methoxyacetyl chloride is reacted to obtain formula IV-1, formula IV-1 is reacted with N-methylallylamine to obtain formula V, and formula V is oxidized to obtain iopromide formula I; method three: using formula II as the starting material, Reaction with allylamine to obtain formula III, reaction of formula III with methoxyacetyl chloride to obtain formula IV-1, reaction of formula IV-1 with 3-methylamino-1,2-propanediol t...
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