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Method for preparing moxifloxacin hydrochloride intermediate

A technology for moxifloxacin hydrochloride and intermediates, which is applied in the field of preparation of moxifloxacin hydrochloride intermediates, can solve the problems of many steps, low yield, cumbersome operation, etc., and achieve the effect of fewer steps, high yield and simple operation

Inactive Publication Date: 2012-04-04
太仓市运通化工厂
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current technology, the difficulty in the synthesis of quinolone antibiotics lies in the side chains. Among them, the synthesis process of the side chains of moxifloxacin is complicated, the operation is cumbersome, there are many steps, and the yield is low.

Method used

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  • Method for preparing moxifloxacin hydrochloride intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 200ml of methylamine into a 500ml three-neck flask, add 80g of 2,3-pyridinedicarboxylic acid while stirring, heat and dissolve slowly until the reaction is refluxed for 48h, TLC detects that the reaction of 2,3-pyridinedicarboxylic acid is complete, cool to room temperature, Slowly poured into ice water, a large amount of solids precipitated while stirring, extracted 3 times with dichloromethane, washed the organic layer with water once, and anhydrous Na 2 SO 4 Drying and concentrating under reduced pressure to dryness yielded 50 g of yellow oil intermediate A with a yield of 75%.

[0021] Dissolve 50g of intermediate A in 375ml of methanol, stir, add 10g of 5% Pd-C, and catalyze hydrogenation in a 1L autoclave at 3Mpa and 65°C for 4h. TLC detects that the reaction of intermediate A is complete, stop heating, and filter out Pd- C, concentrated to dryness under reduced pressure to obtain 45g oil intermediate B.

[0022] Add THF0.45L into a 1L three-neck flask, cool...

Embodiment 2

[0024] Add 550ml of methylamine into a 1L three-necked flask, add 220g of 2,3-pyridinedicarboxylic acid while stirring, heat and dissolve slowly until the reflux reaction is 50h, TLC detects that the reaction of 2,3-pyridinedicarboxylic acid is complete, cool to room temperature, Slowly poured into ice water, a large amount of solids precipitated while stirring, extracted 3 times with dichloromethane, washed the organic layer with water once, and anhydrous Na 2 SO 4 Drying and concentrating under reduced pressure to dryness gave 200 g of yellow oil intermediate A with a yield of 80%.

[0025] Dissolve 200g of intermediate A in 1500ml of methanol, stir, add 40g of 5% Pd-C, and catalyze hydrogenation in a 1L autoclave at 3Mpa, 65°C for 6h. TLC detects that the reaction of intermediate A is complete, stop heating, and filter out Pd- C, concentrated to dryness under reduced pressure to obtain 190g of oil intermediate B.

[0026] Add THF1.9L into a 3L three-neck flask, cool in an...

Embodiment 3

[0028] Add 950ml of methylamine into a 2L three-necked flask, add 380g of 2,3-pyridinedicarboxylic acid while stirring, heat and slowly dissolve until reflux reaction for 48h, TLC detects that the reaction of 2,3-pyridinedicarboxylic acid is complete, cool to room temperature, Slowly poured into ice water, a large amount of solids precipitated while stirring, extracted 3 times with dichloromethane, washed the organic layer with water once, and anhydrous Na 2 SO 4 Drying and concentrating under reduced pressure to dryness gave 362g of yellow oil intermediate A with a yield of 82%.

[0029] Dissolve 362g of intermediate A in 2715ml of methanol, stir, add 72g of 5% Pd-C, and catalyze hydrogenation in a 1L autoclave at 3Mpa, 65°C for 6h. TLC detects that the reaction of intermediate A is complete, stop heating, and filter out Pd- C, concentrated to dryness under reduced pressure to obtain 350g oil intermediate B.

[0030] Add 3.5L THF to a 5L three-neck flask, cool in an ice bat...

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Abstract

The invention discloses a method for preparing a moxifloxacin hydrochloride intermediate, which comprises the following steps of: adding methylamine and 2,3-dipicolinic acid into a reaction vessel to perform a reflux reaction until the 2,3-dipicolinic acid is reacted completely, and carrying out post treatment to obtain an intermediate A; dissolving the intermediate A into alcohol, adding Pd-C with stirring, carrying out catalytic hydrogenation in a high pressure kettle with a pressure of 3Mpa and a temperature of 65 DEG C until the intermediate A is reacted completely, and carrying out post treatment to obtain an intermediate B; and adding tetrahydrofuran into the reaction vessel, carrying out ice-bath cooling to a temperature of below 5 DEG C, adding sodium borohydride and boron fluoride etherate, controlling a temperature in a range of below 15 DEG C, adding the intermediate B, performing a reflux reaction until the intermediate B is reacted to be disappeared, and carrying out post treatment to obtain an intermediate C. The method for preparing the moxifloxacin hydrochloride intermediate, which is provided by the invention, is simple to operate and has few steps and high yield, and the industrial production is easy to realize.

Description

technical field [0001] The invention relates to the field of synthesis of pharmaceutical intermediates, in particular to a method for preparing a moxifloxacin hydrochloride intermediate. Background technique [0002] Moxifloxacin hydrochloride is a broad-spectrum and 8-methoxyfluoroquinolone antibacterial drug with antibacterial activity. Moxifloxacin hydrochloride has shown broad-spectrum antibacterial activity in vitro against Gram-positive bacteria, Gram-negative bacteria, anaerobic bacteria, acid-fast bacteria and atypical microorganisms such as Mycoplasma, Chlamydia and Legionella. There are many dosage forms of moxifloxacin hydrochloride, the market consumption is large, and the prospect is broad. In the current technology, the difficulty in the synthesis of quinolone antibiotics lies in the side chains. Among them, the synthesis process of the side chains of moxifloxacin is complicated, with cumbersome operations, many steps, and low yields. Contents of the inventi...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 张卫东
Owner 太仓市运通化工厂
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