Preparation of pimobendan key intermediate

A technology of nitrophenyl and oxo substitution, which is applied in the direction of organic chemistry and can solve problems that are not conducive to industrial production

Active Publication Date: 2016-09-28
WISDOM PHARM CO LTD
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

This method is unfavorable for suitability for suitability for indust

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  • Preparation of pimobendan key intermediate
  • Preparation of pimobendan key intermediate
  • Preparation of pimobendan key intermediate

Examples

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Embodiment

[0021] 1. Preparation of N-(2-nitro-4-propionylphenyl)acetamide (formula I)

[0022] h 2 SO 4 (200mL) and nitric acid (600mL) were mixed and cooled to below 0°C, then N-(4-propionylphenyl)acetamide (200g, 1.05mol) was added in batches, and the internal temperature of the system was kept below 0 °C for 5 hours. The reaction solution was slowly poured into a mixture of ice water (2000 g) and dichloromethane (2000 mL), stirred for 30 min, and the organic phase was separated after the ice completely turned into water. The aqueous phase was extracted with dichloromethane (800 mL). The organic phases were combined and washed twice with saturated brine (2×2000 mL). After the solvent was removed under reduced pressure, the residue was recrystallized from heptane / ethyl acetate to obtain a pale yellow solid (192 g, 77%).

[0023] 2. Preparation of N-(4-(2-bromopropionyl)-2-nitrophenyl)acetamide (formula II)

[0024] N-(2-nitro-4-propionylphenyl)acetamide (150g, 0.63mol) was added t...

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Abstract

The invention relates to a preparation technology of a pimobendan key intermediate 6-(4-amino-3-nitro phenyl)-5-methyl-4, 5-dihydrogen pyridazine-3(2H)-ketone (formula V). The preparation technology is short in synthesis route and simple in operation, thus having large industrial production prospect. The chemical reaction formula is shown in the description.

Description

technical field [0001] The invention relates to the preparation of a key intermediate of pimobendan-6-(4-amino-3-nitrophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one. Background technique [0002] Pimobendan (Pimobendan, UD-CG115BS, Acardi, CAS: 74150-27-9) was developed by Boehringer Ingelheim in Germany and first listed in Japan in 1994 as a cardiotonic drug with vasodilation. Diesterase inhibitors are mainly used clinically for the treatment of heart failure. The mechanism of action of this drug is different from that of traditional cardiotonic drugs, and its positive inotropic effect is mainly attributed to the enhancement of the effect of cardiac contractile proteins on Ca 2+ Sensitivity and inhibitory effect on phosphodiesterase III (PDEIII), it is the first calcium sensitizer drug on the market. The chemical name of this product is: 4,5-dihydro-6-[2-(4-methoxyphenyl)-1H-benzimidazol-5-yl]-5-methyl-3(2H)- Pyridazinone has the following chemical structural formula: ...

Claims

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Application Information

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IPC IPC(8): C07D237/04
CPCC07D237/04
Inventor 邱小龙张义森邹平王东辉邓贤明游正伟江中兴胡林曹雷
Owner WISDOM PHARM CO LTD
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