Preparation method of isavuconazole intermediate

A technology for isavuconazole and intermediates, which is applied in the field of preparation of isavuconazole intermediates, and can solve the problems of unsuitable for large-scale industrial production, complex preparation process, and high cost of raw materials

Inactive Publication Date: 2016-07-06
KBP BIOSCIENCES CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The existing preparation process of isavuconazole intermediate (formula 1) is complex, the

Method used

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  • Preparation method of isavuconazole intermediate
  • Preparation method of isavuconazole intermediate
  • Preparation method of isavuconazole intermediate

Examples

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Embodiment

[0065] Example 4-(2-((2R,3R)-3-(2,5-difluorophenyl)-3-hydroxyl--4-(1H-1,2,4-triazol-1-yl ) butane -2-yl) thiazol-4-yl) preparation of benzonitrile (formula 1)

[0066]

[0067] (1) Preparation of 2,5-difluorobenzoic acid methyl ester (formula 3)

[0068] 2,5-difluorobenzoic acid (31.6g, 0.2mol) and thionyl chloride (35.7g, 0.3mol) were dissolved in 500mL of methanol, and the reaction was heated under reflux until the reaction was completed. After cooling, ice water was added, extracted with ethyl acetate, and the organic phase was dried and concentrated to obtain 31.2 g of product with a yield of 90.7%.

[0069] (2) Preparation of 3-(2,5-difluorophenyl)-2-methyl-3-oxopropionitrile (formula 4)

[0070] Dissolve methyl 2,5-difluorobenzoate (31.2g, 0.18mol), sodium ethoxide (14.7g, 0.22mol) and propionitrile (11.9g, 0.22mol) in 100mL of ethanol, heat the reaction to the end, and The solvent was concentrated to the remaining 20 mL, water was added, and extracted with ethy...

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Abstract

The invention belongs to the technical field of chemical drug intermediate preparation and relates to a preparation method of an isavuconazole intermediate. The preparation method is a 4-(2-((2R, 3R)-3-(2, 5-difluorophenyl)-3-hydroxy-4-(1H-1, 2, 4-triazole-1-yl)butane-2-yl)thiazole-4-yl)benzontrile preparation method. The 4-(2-((2R, 3R)-3-(2, 5-difluorophenyl)-3-hydroxy-4-(1H-1, 2, 4-triazole-1-yl)butane-2-yl)thiazole-4-yl)benzontrile has a structural formula (I) shown in the description.

Description

1. Technical field [0001] The invention belongs to the technical field of preparation of chemical drug intermediates, in particular to a preparation method of isavuconazole intermediates, namely 4-(2-((2R,3R)-3-(2,5-difluorophenyl )-3-Hydroxy-4-(1H-1,2,4-triazol-1-yl)butane-2-yl)thiazol-4-yl)benzonitrile preparation method. 2. Background technology [0002] The incidence of invasive fungal infections has increased steadily over the past 20 years. With the increase in the number of patients with compromised immune systems such as chemotherapy, transplantation, HIV / AIDS infection, or diabetes, the incidence of fungal infections is increasing, and some fungal infections have a high fatality rate. fungal drugs. Isavuconazole is the latest triazole antifungal drug developed by Roche. Its mechanism of action is to inhibit the key enzyme of ergosterol biosynthesis on the fungal cell membrane - sterol 14a-demethylase, thereby destroying the integrity of the membrane and affecting ...

Claims

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Application Information

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IPC IPC(8): C07D417/06
Inventor 王爱臣李丽
Owner KBP BIOSCIENCES CO LTD
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