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A kind of synthetic method of 6-hydrazino-1h-pyrazolo[3,4-b]pyridine and its downstream products

A synthetic method, the technology of pyrazolo, which is applied in the field of organic chemical intermediate synthesis, can solve the problems of unsuitable scale-up and low reaction yield, and achieve the effects of less by-products, simple synthesis steps and mild reaction conditions

Active Publication Date: 2020-06-26
上海毕得医药科技股份有限公司
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Problems solved by technology

[0007] The object of the present invention is to provide a kind of synthetic method of 6-hydrazino-1H-pyrazolo[3,4-b]pyridine, and then through 6-hydrazino-1H-pyrazolo[3,4-b]pyridine The method for synthesizing 6-bromo-1H-pyrazolo[3,4-b]pyridine solves the low reaction yield of the final product 6-bromo-1H-pyrazolo[3,4-b]pyridine in the prior art, Technical flaws that should not be magnified

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  • A kind of synthetic method of 6-hydrazino-1h-pyrazolo[3,4-b]pyridine and its downstream products
  • A kind of synthetic method of 6-hydrazino-1h-pyrazolo[3,4-b]pyridine and its downstream products
  • A kind of synthetic method of 6-hydrazino-1h-pyrazolo[3,4-b]pyridine and its downstream products

Examples

Experimental program
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Effect test

Embodiment 1

[0040] In n-butanol, add 2,6-dichloro-3-pyridinecarbaldehyde (1056g, 6.0mol, 1eq.) and hydrazine hydrate (1767g, 30.0mol, 5.0eq., 85%), then, stir at room temperature After 0.5h, heat up to reflux overnight, cool and filter, and collect the filter cake, which is compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine (776g, 5.2mol), yield It was 87%, and the product color was white solid.

[0041] Take a trace amount of compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine for H NMR determination, where the abscissa represents the chemical shift, the ordinate represents the peak intensity, and the combined figure 1 Obtain the spectrogram of compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine, 1 H NMR(600MHz,DMSO)δ12.76(s,1H), 7.95(s,1H),7.81–7.60(m,2H),6.46(d,J=8.7Hz,1H),4.22(s,2H) .

[0042] Further use the compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine prepared above to further prepare the compound (3) 6-bromo-1H-pyrazolo[3,4-b] pyridine.

[0043] At room temperature, co...

Embodiment 2

[0046] In n-butanol, 2,6-dichloro-3-pyridinecarbaldehyde (1056 g, 6.0 mol, 1 eq.) and hydrazine hydrate (1414 g, 24.0 mol, 4 eq., 85%) were added. Then, it was stirred at room temperature for 0.5 h. Afterwards, the temperature was raised to reflux overnight. After cooling and filtering, the filter cake was collected, which was compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine (698g, 4.7mol). The yield was 78%, and the color of the product was white solid.

[0047] At room temperature, compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine (about 698g, 4.7 mol, 1eq.) was dissolved in chloroform, and then liquid bromine (1502g, 9.4mol, 2.0eq.), and keep the temperature at 40°C, after the dropwise addition of liquid bromine is completed, heat to reflux for 3h, and after cooling to room temperature, slowly add saturated sodium bicarbonate solution dropwise under ice bath conditions to extract the reaction , and then added dichloromethane, liquid separation extraction. The organi...

Embodiment 3

[0049] In n-butanol, 2,6-dichloro-3-pyridinecarbaldehyde (1056 g, 6.0 mol, 1 eq.) and hydrazine hydrate (2120 g, 36.0 mol, 6 eq., 85%) were added. Then, it was stirred at room temperature for 1.0 h. Afterwards, the temperature was raised to reflux overnight. After cooling and filtering, the filter cake was collected, which was compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine (716g, 4.8mol), the yield was 80%, and the product color was white solid.

[0050] At room temperature, compound (2) 6-hydrazino-1H-pyrazolo[3,4-b]pyridine (about 716g, 4.8 mol, 1eq.) was dissolved in chloroform, and then liquid bromine (1534g, 9.6mol, 2.0eq.), and keep the temperature at 40°C, after the dropwise addition of liquid bromine is completed, heat to reflux for 3h, after cooling to room temperature, slowly add saturated sodium bicarbonate solution dropwise under ice bath conditions to extract the reaction , and then added dichloromethane, liquid separation extraction. The organic layer was...

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Abstract

The invention discloses a synthetic method of 6-hydrazino-1H-pyrazolo[3,4-b]pyridine and a downstream product thereof, and relates to the technical field of the organic chemical industry intermediatesynthesis. The synthetic method of the 6-hydrazino-1H-pyrazolo[3,4-b]pyridine comprises the following steps: firstly using easily obtained 2,6-dichloro-3-pyridylaldehyde and hydrazine hydrate as raw materials, to obtain the 6-hydrazino-1H-pyrazolo[3,4-b]pyridine, and using the 6-hydrazino-1H-pyrazolo[3,4-b]pyridine to synthesize the downstream product of 6-bromo-1H-pyrazolo[3,4-b]pyridine thereof.The synthetic method is capable of solving problems of preparing the 6-bromo-1H-pyrazolo[3,4-b]pyridine in the prior art that the raw materials are expensive and the yield is low. The route is mild in reaction condition, simple in follow-up operation, and environmentally friendly. A product is prepared in the higher yield and high purity, and the method is suitable for industrialized technology amplification.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic chemical intermediates, in particular to a method for synthesizing 6-hydrazino-1H-pyrazolo[3,4-b]pyridine and its preparation of 6-bromo-1H-pyrazolo[3 , The synthetic method of 4-b] pyridine. Background technique [0002] Indazole, also known as benzopyrazole or isoindone, is an aromatic compound. In recent years, indazole derivatives have been found to have a wide range of biological activities, such as anti-inflammatory, anti-HIV, anti-hypertensive, anti-microbial and anti-tumor activities. The indazole skeleton has been applied to construct a variety of molecules or inhibitors with pharmaceutical activity, which has strong pharmacological significance. Drugs such as pazopanib, axitinib, and niraparib, which contain an indazole skeleton, have been approved for the treatment of cancer. Related documents also report that indazole derivatives are used in the treatment of diseases th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 张锐豪
Owner 上海毕得医药科技股份有限公司
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