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Preparation method for 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester

A dicarboxylic acid diester, tert-butyl technology, applied in 6-tert-butyl-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-3, The field of preparation of -6(7H)-dicarboxylic acid diester can solve the problems such as no suitable industrial synthesis method, and achieve the effects of convenient operation, high yield and easy reaction

Inactive Publication Date: 2013-05-01
上海药明康德新药开发有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Preparation method for 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester
  • Preparation method for 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester
  • Preparation method for 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester

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Experimental program
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Embodiment 1

[0016] Embodiment 1: a, N-Boc-3-piperidone (2.99 g, 15 mmol) and ethyl diazoacetate (1.72 g, 15 mmol) were placed in anhydrous tetrahydrofuran (20 mL), under nitrogen protection at -78 o C, LDA ((15 mL, 1 M in THF) solution was added dropwise, and reacted at this temperature for 4 hours, acetic acid (1.5 mL) quenched the reaction, and stirred at room temperature for one hour, the reaction solution was poured into water (40 mL), extracted with isopropyl ether (20 mL), and the organic phase was extracted with 5% NaHCO 3 Washed, dried over anhydrous sodium sulfate, and concentrated to obtain the crude compound 2 (4 g), used directly in the next step.

[0017] Compound 2 (4 g) and pyridine (8 mL) were dissolved in isopropyl ether (15 mL), and phosphorus oxychloride (2.3 g, 15 mmol) was added dropwise under ice cooling, and the reaction solution was stirred at room temperature for 8 hours, hydrogen Sodium oxide solution (5 mL, 0.1M) was added to the reaction solution, extracted ...

Embodiment 2

[0022] Example 2: N-Boc-3-piperidone (29.9 g, 150 mmol) and ethyl diazoacetate (17.2 g, 150 mmol) were placed in anhydrous tetrahydrofuran (200 mL), under nitrogen protection at -78 o C, LDA ((150 mL, 1 M in THF) solution was added dropwise, and reacted at this temperature for 4 hours, acetic acid (15 mL) quenched the reaction, and stirred at room temperature for 1 hour, the reaction solution was poured into water (400 mL), extracted with isopropyl ether (200 mL), and the organic phase was extracted with 5% NaHCO 3 Washed, dried over anhydrous sodium sulfate, and concentrated to obtain the crude compound 2 (42 g), used directly in the next step,

[0023] Dissolve compound 2 (42 g) and pyridine (80 mL) in isopropyl ether (150 mL), add phosphorus oxychloride (23 g, 150 mmol) dropwise under ice-cooling, and stir the reaction solution at room temperature for 8 hours, hydrogen Sodium oxide solution (50 mL, 0.1M) was added to the reaction solution, extracted with ethyl acetate (...

Embodiment 3

[0026] Example 3: N-Boc-3-piperidone (299 g, 1.5 mol) and ethyl diazoacetate (172 g, 1.5 mol) were placed in anhydrous THF (2 L), under nitrogen protection at -78 o C, dropwise add LDA ((1.5 L, 1 M in THF) solution, and react overnight at this temperature, quench the reaction with acetic acid (150 mL), and stir at room temperature for 1 hour, the reaction solution is poured into water (3 L ), extracted with isopropyl ether (1.5 L), and the organic phase was extracted with 5% NaHCO 3 Washed, dried over anhydrous sodium sulfate, and concentrated to obtain the crude compound 2 (440 g), used directly in the next step.

[0027] Dissolve compound 2 (440 g) and pyridine (800 mL) in isopropyl ether (1.5 L), add phosphorus oxychloride (230 g, 1.5 mol) dropwise under ice-cooling, stir the reaction solution at room temperature overnight, and Sodium solution (500 mL, 0.1M) was added to the reaction solution, extracted with ethyl acetate (300 mL X 3), the organic phase was washed with ...

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Abstract

The invention relates to a preparation method for 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester. The invention mainly aims to solve the technical problem that a suitable industrial synthesis method does not exist at present. The reaction formula of the preparation method is shown as follows: , the 6-tert-butyl-3-ethyl-4, 5-dihydro-1H-pyrazolo-[3, 4-c] pyridine-3, -6 (7H)-dicarboxylic acid diester and related derivatives obtained by the invention have important applications in medicinal chemistry and organic synthesis.

Description

technical field [0001] The present invention relates to the preparation of 6-tert-butyl-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-3,-6(7H)-dicarboxylic acid diester method. Background technique [0002] 6-tert-butyl-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-3,-6(7H)-dicarboxylic acid diester and related derivatives It has important applications in medicinal chemistry and organic synthesis and has excellent prospects. The synthesis of 6-tert-butyl-3-ethyl-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-3,-6(7H)-dicarboxylic acid diester is difficult at present . Therefore, it is of great significance to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a kind of 6-tert-butyl-3-ethyl-4,5-dihydro-1H-pyrazolo [3,5-dihydro-1H-pyrazolo [3, 4-c] Synthesis of pyridine-3,-6(7H)-dicarboxylic acid diesters. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 杨彩民毛延军陈琳琳唐小伍钱国磊赵洪宾李继成崔娣于凌波
Owner 上海药明康德新药开发有限公司