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Preparation method of vadadustat
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A technology of valdurostat and methyl picolinate, applied in the field of preparation of valdurostat, can solve the problems of harsh reaction conditions, high cost, unfavorable enlarged production and the like
Active Publication Date: 2020-03-24
SUNSHINE LAKE PHARM CO LTD
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[0014] 1. There are strong acid conditions in the route, which has high requirements on the reaction vessel, which is not conducive to the expansion of production
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Embodiment 1
[0048] Example 1 Synthesis of 3,5-dichloro-2-pyridinecarboxylic acid methyl ester
[0049] Add the compound 3,5-dichloro-2-pyridinecarboxylic acid (1.92g), concentrated sulfuric acid (0.19mL), methanol (19mL) into the reaction flask at room temperature, control the temperature at 65°C, reflux for 6h, the reaction is complete, the reaction solution Concentrate to dryness under reduced pressure at 40°C, add water (19 mL) to wash twice, filter and dry with suction to obtain 1.71 g of methyl 3,5-dichloro-2-picolinate, yield 83.0%.
[0052] Example 2 Synthesis of 3,5-dichloro-2-pyridinecarboxylic acid methyl ester
[0053] Add the compound 3,5-dichloro-2-pyridinecarboxylic acid (38.4g), concentrated sulfuric acid (3.8mL), methanol (384mL) into the reaction flask at room temperature, control the temperature at 65°C, reflux for 6h, the reaction is complete, the reaction solution Concentrate under reduced pressure to dryness at 40°C, add water to wash twice, and dry to obtain 3,5-dichloro-2-picolinic acid methyl ester 38.5g, yield 93.4%.
Embodiment 3
[0054] Example 3 Synthesis of 5-(3-chlorophenyl)-3-chloropyridine-methyl formate
[0055] Add compound 3,5-dichloro-2-pyridinecarboxylic acid methyl ester (1.03g), 3-chlorophenylboronic acid (0.86g), K2CO3 (0.87g), PdCl 2 (dppf) (0.04g), DMF (10mL) and H2O (1mL), after nitrogen replacement, react at a temperature of 45°C for 22h, the reaction is complete, add water and ethyl acetate to the reaction solution to extract twice, and then wash the organic phase with water Once, recrystallized with n-hexane and ethyl acetate to finally obtain 1.01 g of white solid 5-(3-chlorophenyl)-3-chloropyridine-methyl carboxylate with a yield of 71.9%.
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Abstract
The invention provides a preparation method of vadadustat, and belongs to the field of pharmaceutical chemical industry. The method comprises the following steps: mixing 3,5-dichloro-2-picolinic acid,methanol and sulfuric acid at a certain temperature, and carrying out a reaction to obtain 3,5-dichloro-2-picolinic acid methyl ester; adding 3-chlorophenylboronic acid, and carrying out a catalyticreaction to obtain 5-(3-chlorphenyl)-3-chloropyridine-methyl formate; and adding glycine into the 5-(3-chlorphenyl)-3-chloropyridine-methyl formate, and carrying out a reaction to obtain the 5-(3-chlorphenyl)-3-chloropyridine-methyl formate. The method has the characteristics of high product purity, high yield, low cost, simple operation and stable process.
Description
technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of valdurestat. Background technique [0002] Vadadustat is a novel titratable oral hypoxia-inducible factor prolyl hydroxylase (HIF-PH) inhibitor currently being developed for the treatment of anemia. Vadadustat utilizes the same mechanism of action that the body uses to naturally adapt to low oxygen levels like those caused by increased altitude. At higher altitudes, the body's response to a hypoxic environment is an increase in HIF, which coordinates the interdependent processes of iron mobilization and erythropoietin production to increase red blood cell production and ultimately oxygen delivery. [0003] Currently, Vadadustat is in Phase III clinical trials worldwide. [0004] Vadadustat (Vadadustat), the structural formula is as follows: [0005] [0006] US20070299086 discloses the preparation method of Vadadustat (Vadadustat), speci...
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