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Preparation method of 2 (2-ethoxy-2-oxoethyl)-8-methyl-5, 6-dihydroimidazo pyrazine carboxylic acid tert-butyl ester

A technology of tert-butyl carboxylate and oxoethyl, applied in 2(2-ethoxy-2-oxoethyl)-8-methyl-5,6-dihydroimidazopyrazinecarboxylic acid In the field of preparation method of tert-butyl ester, it can solve the problems that there are no synthetic methods reported in the literature, and achieve the effects of reasonable reaction process design, easy reaction and convenient operation

Active Publication Date: 2017-11-03
SHANGHAI SYNTHEALL PHARM CO LTD +4
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Problems solved by technology

Mainly solve the technical problems that there is no synthesis method reported in the literature

Method used

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  • Preparation method of 2 (2-ethoxy-2-oxoethyl)-8-methyl-5, 6-dihydroimidazo pyrazine carboxylic acid tert-butyl ester

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Effect test

Embodiment 1

[0012] Compound 1 (500 g, 1.92 mol) and ammonia water (5.5 L) were placed in a 10 L autoclave, and reacted at 160°C for 24 hours, TLC or LCMS showed that the reaction was complete. The reaction solution was cooled, filtered to obtain a white solid, and the remaining reaction solution was extracted with ethyl acetate (1.5 L x 5), the extracts were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain a white solid and the filtered solid, and dried in vacuo to obtain Crude compound 2 (420 g).

[0013] Compound 2 (180.00 g, 1.65 mol,) and ethyl 4-oxobut-2-enoate (221.91 g, 1.73 mol,) were dissolved in anhydrous acetonitrile (2 L), heated to 80°C for 12 hours . LCMS detected that the reaction was complete. The reaction solution was concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (gradient elution: petroleum ether to petroleum ether / ethyl acetate volume ratio = 100 / 1) to o...

Embodiment 2

[0018] Embodiment 2, the first step reaction time is 48 hours, the second step reaction temperature is 75 DEG C, the reaction time is 24 hours, the third step reaction temperature is 60 DEG C, all the other are the same as embodiment 1.

Embodiment 3

[0019] Embodiment 3, the first step reaction time is 72 hours, the second step reaction temperature is 70 DEG C, the reaction time is 18 hours, the third step reaction temperature is 50 DEG C, all the other are the same as embodiment 1.

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Abstract

The invention relates to a synthesizing method of 2 (2-ethoxy-2-oxoethyl)-8-methyl-5, 6-dihydroimidazo [1, 2-a] pyrazine-7 (8H)-carboxylic acid tert-butyl ester, and aims at solving the technical problem that a proper industrial synthesizing method is not provided currently. The method comprises the following four steps: 1, reacting a compound 1 and ammonium hydroxide in a high-pressure kettle to obtain a compound 2; 2, reacting the compound 2 and 4-epoxide-2-ethyl crotonate through acetonitrile to obtain a compound 3; 3, hydrogenating the compound 3 through a catalyst which is palladium / carbon in methanol to obtain a compound 4; and 4, adding Boc anhydride and potassium carbonate to the compound 4 in ethyl alcohol; and reacting overnight at room temperature to obtain a final compound 5.

Description

technical field [0001] The present invention relates to the preparation method of 2(2-ethoxyl-2-oxoethyl)-8-methyl-5,6-dihydroimidazopyrazinecarboxylic acid tert-butyl ester, namely compound 2-(2- Synthesis of ethoxy-2-oxoethyl)-8-methyl-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-tert-butyl carboxylate. Background technique [0002] Compound 2-(2-ethoxy-2-oxoethyl)-8-methyl-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-tert-butylcarboxylate Esters (no CAS number, may prove to be existing compounds in the future) and related derivatives are widely used in medicinal chemistry and organic synthesis. tert-butyl 2-(2-ethoxy-2-oxoethyl)-8-methyl-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-carboxylate present There is no literature report on the synthesis method of ester. 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...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 毛延军唐小伍郭泽民何米娜蒋欣欣鲍微泽吴东平袁超伟李红于凌波马汝建
Owner SHANGHAI SYNTHEALL PHARM CO LTD
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