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Preparation method of Plerixafor

A Plerixafor and structural formula technology, applied in the direction of organic chemistry, can solve problems such as difficult removal, incomplete reaction, and reduced activity

Inactive Publication Date: 2012-09-05
朱靖华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When using ethyl trifluoroacetate for protection, due to the strong polarity of the trifluoroacetyl group, the activity of the fourth unprotected -NH is reduced, and the subsequent reaction cannot be completely reacted, thus introducing a difficult-to-remove NH after further deprotection. Impurity 1,4,8,11-tetraazacyclotetradecane

Method used

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  • Preparation method of Plerixafor
  • Preparation method of Plerixafor
  • Preparation method of Plerixafor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Implementation Example 1: Preparation of 3Boc-protected 1,4,8,11-tetraazacyclotetradecane

[0048] Take 10g (0.05mol) of 1,4,8,11-tetraazacyclotetradecane, add 50ml of acetone-water (2:1), add 10.119g (0.1mol) of triethylamine, diisopropylethylamine 3.225 g (0.025 mol), 38.194 g (0.175 mol) of di-tert-butyl carbonate was added dropwise at room temperature, stirred at room temperature for 24 hours after the dropwise addition, and the reaction was monitored by HPLC. After the reaction was completed, the reaction was evaporated to dryness at 50°C under reduced pressure to obtain a light yellow oil, which was applied to a 150 g silica gel column and eluted with ethyl acetate. The ethyl acetate solution was collected and evaporated to dryness under reduced pressure to obtain 23.12 g of a white foam. 92.36%. 1 HNMR (400MHz, CDCl 3 , δppm): 1.74 (2H, q, 5.5); 1.96 (2H, q, 6.5); 2.66 (2H, t, 5.5); 2.82 (2H, t, 5.5); 3.33 (4H, m); , m); 3.37 (2H, m), 3.43 (4H, m).

Embodiment 2

[0049] Implementation Example 2: Preparation of 6Boc-protected Plerixafor

[0050]Take 20.03g (0.04mol) of 3Boc-protected 1,4,8,11-tetraazacyclotetradecane, dissolve it in 400ml of anhydrous acetonitrile, add 20g of anhydrous potassium carbonate, 3.5012g of α-α'dichloroxylene (0.02mol), sodium iodide 75mg, refluxed under nitrogen protection for 24 hours, and TLC monitored the reaction. After completion of the reaction, let cool to room temperature, filter with suction, wash the filter cake with 200ml of acetonitrile, combine the acetonitrile solution, and evaporate to dryness under reduced pressure to obtain 21.20 g of 6Boc-protected plerixafor with a yield of 96.06%. Recrystallized with ethanol-water mixed solvent to obtain a white solid.

Embodiment 3

[0051] Implementation Example 3: Plerixafor·8HCl·3H 2 O compound preparation

[0052] Take 20 g of 6Boc-protected plerixafor, add 200 ml of methanol, stir to dissolve, add 60 ml of concentrated hydrochloric acid dropwise at room temperature, stir at room temperature for 48 hours after the dropwise addition, and monitor the reaction by TLC. After the reaction was completed, it was filtered with suction, and the filter cake was dried under reduced pressure at 50° C. to obtain 13.54 g of white solid, with a yield of 88.04%.

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Abstract

The invention relates to a preparation method of Plerixafor. The preparation method comprises the following steps: carrying out selective three-protection on 1,4,8,11-tetraazacyclotetradecane using di-tert-butyl carbonate, carrying out a reaction on the three-protection product and dihalide substituted xylene to obtain Boc protecting Plerixafor, and carrying out gentle deprotection under the action of concentrated hydrochloric acid to prepare Plerixafor. By using the method provided by the invention to prepare Plerixafor, advantages are as follows: the reaction condition is gentle, the process controllability is good, solvent with low toxicity and good safety is used, the final product has high purity, the cost is low and the like.

Description

technical field [0001] The present invention relates to a preparation method of plerixafor. Background technique [0002] Plerixafor is a major advance in the treatment of patients with certain types of cancer who require stem cell transplants. Because this product is beneficial to patients, doctors and transplant treatment centers will become an integral part of the stem cell transplant treatment plan. In order to perform stem cell transplantation, approximately 2 million stem cells / kg must be collected based on body weight. Many patients take anywhere from 3-4 hours to several days to complete the process. Some patients even do not mobilize enough stem cells to be transplanted. For many cancer patients, mobilizing stem cells is the only hope for shrinking cancer or curing it. [0003] Plerixafor, chemical name: 1,1'-[1,4-phenylene bis(methylene)]-di-1,4,8,11-tetraazacyclotetradecane , and its molecular structure is as follows: [0004] [0005] In relevant synthet...

Claims

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Application Information

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IPC IPC(8): C07D403/10C07D257/02
Inventor 朱靖华
Owner 朱靖华
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