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Synthetic method of 5-(boc t-butoxycarbonyl)-1-methyl-imidazopyridine-7-carboxylic acid

A technology of tert-butylcarbonyl and synthetic method, which is applied in the field of synthesis of 5-(tert-butylcarbonyl)-1-methyl-imidazopyridine-7-carboxylic acid, can solve problems such as no suitable industrial synthesis method, To achieve the effect of reasonable reaction process design, easy reaction and short route

Inactive Publication Date: 2017-09-22
WUXI APPTEC (TIANJIN) CO LTD
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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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  • Synthetic method of 5-(boc t-butoxycarbonyl)-1-methyl-imidazopyridine-7-carboxylic acid

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Embodiment

[0012] In the first step, compound 1 (50.0 g, 235.7 mmol) was dissolved in methanol (800 mL), triethylamine (180 mL) and Pd(dppf) were added 2 Cl 2 (8.00 g), stirred at 50 degrees Celsius for 12 hours under carbon monoxide pressure of 50 psi, added H after removing the solvent under reduced pressure 2 O ( 200 mL ) was dissolved, extracted with ethyl acetate (500 mL x 4), the combined organic phases were dried over anhydrous sodium sulfate, and the filtrate was concentrated to obtain compound 2 (73.00 g) as a yellow oil, and the crude product was directly used in the next step.

[0013] In the second step, compound 2 ( 19.00 g, 99.38 mmol ) was dissolved in methanol (500 mL), concentrated HCl ( 40 mL) and Pd / C (10.00 g) were added, and the reaction was carried out at 50°C for 12 hours under a hydrogen pressure of 50 psi. LC -MS monitored the reaction to be complete, filtered, and concentrated the filtrate to obtain compound 3 (73.00 g) as a yellow solid.

[0014] Step 3: Dis...

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Abstract

The invention relates to a synthetic method of 5-(boc t-butoxycarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo-[4,5-c]pyridine-7-carboxylic acid, and mainly aims to solve the technical problem that a method suitable for industrial synthesis is unavailable at present. The synthetic method comprises the four steps: I, performing a carbonyl inserting reaction under the catalysis of palladium to obtain a compound 2; II, hydrogenating the compound 2 under the catalysis of strong hydrochloric acid to obtain a compound 3; III, reacting the compound 3 with BOC acid anhydride under a triethylamine alkaline condition to obtain a compound 4; IV, hydrolyzing the compound 4 with sodium hydroxide to obtain a compound 5. The chemical reaction formula is shown in the description.

Description

technical field [0001] The invention relates to a synthesis method of compound 5-(tert-butylcarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-7-carboxylic acid. Background technique [0002] Compound 5-(tert-butylcarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-7-carboxylic acid (CAS: 1823981-06- 1) and related derivatives are widely used in medicinal chemistry and organic synthesis. There are few reports on the synthesis of 5-(tert-butylcarbonyl)-1-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-7-carboxylic acid . Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of the invention is to develop a kind of 5-(tert-butylcarbonyl)-1-methyl-4,5,6,7-tetrahydro- Synthetic method of 1H-imidazo[4,5-c]pyridine-7-carboxylic acid. It mainly so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 张大为周强赵红双高明飞于智宇姚宝元卢荣昌白有银孙春刘雨雷韩华欣付新雨卢仔倚李旭东于凌波马汝建
Owner WUXI APPTEC (TIANJIN) CO LTD
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