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Synthesis method of 2-oxo-pyrido[2,3-d]azepin-7(2H)-tert-butyl formate

A technology of tert-butyl formate and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of no industrial synthesis method, etc., and achieve the effect of reasonable reaction process design, convenient operation and easy reaction

Inactive Publication Date: 2019-04-12
上海药明康德新药开发有限公司
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Problems solved by technology

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

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  • Synthesis method of 2-oxo-pyrido[2,3-d]azepin-7(2H)-tert-butyl formate

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[0011] Step 1: Dissolve 100 grams of compound 1 and 24.15 grams of potassium carbonate in 1.2 liters of acetonitrile, add compound 2 at 10°C, then stir at room temperature for two hours, TLC (petroleum ether: ethyl acetate = 3:1) It shows that compound 1 is completely reacted. The reaction solution was filtered, the mother liquor was spin-dried, and the crude product was purified by silica gel column chromatography to obtain 50 g of compound 3, yield: 42.7%.

[0012] The second step: 2.5 g of compound 3 was dissolved in 12 mol / L hydrochloric acid, and then reacted at 130° C. for 14 hours. Gas phase mass spectrometry showed that the reaction was complete. The solvent was spin-dried under reduced pressure, and the crude product was directly used in the next step. The yield is 100%.

[0013] The third step: 16 grams of compound 4 and 16.16 grams of triethylamine were dissolved in 150 milliliters of dichloromethane, and 19 grams of Boc 2 O, the addition was complete, and stirre...

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Abstract

The invention relates to a synthesis method of 2-oxo-pyrido[2,3-d]azepin-7(2H)-tert-butyl formate, and mainly solves the technical problem that no suitable industrial synthesis method exists at present. The method comprises the following three steps: step 1, in the presence of potassium carbonate, a compound 1 reacts with 3-cyano propyne in an ethanol solvent to obtain a compound 3; step 2, hydrolysis and cyclization are carried out on the compound 3 in concentrated hydrochloric acid to obtain a compound 4; and step 3, the compound 4 and triethylamine are dissolved in dichloromethane, and Boc2O is added for protecting amino to obtain a compound 5, wherein a reaction formula is as the follows.

Description

technical field [0001] The present invention relates to a method for synthesizing tert-butyl 2-oxyylidene-pyrido[2,3-d]azepine-7(2H)-formate, that is, the compound 2-oxyylidene-5,6,8, Synthesis method of 9-tetrahydro-1H-pyrido[2,3-d]azepine-7(2H)-carboxylic acid tert-butyl ester. Background technique [0002] Compound 2-Oxylidene-5,6,8,9-tetrahydro-1H-pyrido[2,3-d]azepine-7(2H)-carboxylic acid tert-butyl ester (CAS: 1003589-96-5 ) and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthetic methods of the compound 2-oxyylidene-5,6,8,9-tetrahydro-1H-pyrido[2,3-d]azepine-7(2H)-tert-butyl carboxylate. Therefore, it is necessary to develop a synthetic method with readily available raw materials, convenient operation, easy control of the reaction, and suitable overall yield. Contents of the invention [0003] The purpose of the present invention is to develop a compound 2-oxygenide-5,6,8,9-tetrahydro...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 张大为周强白有银高明飞付新雨姚宝元谭汝鹏孔祥南刘鲜赵廷王曦孙春卢荣昌刘雨雷魏昕睿于凌波马汝建
Owner 上海药明康德新药开发有限公司
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