CN111808102B - 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride and synthetic method thereof - Google Patents
3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride and synthetic method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of organic synthesis, and discloses 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride and a synthesis method thereof. The method comprises the following steps: the 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride is prepared by taking 5-methoxypyridine-2, 3-dicarboxylic acid as a raw material and carrying out six-step reactions of substitution, reduction, substitution, cyclization, substitution and cyclization. Provides a high-efficiency synthesis method for the synthesis of the compound.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and relates to 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride and a synthesis method thereof.
Background
Pyridine and its derivatives are fine chemical products with high added value, and play an important role in the production of medicines, pesticides, perfumes, dyes, surfactants, rubber aids, feed additives and the like. In recent years, the field of application of pyridine and its derivatives has been expanding. At present, pyridine and derivatives thereof in China depend on import, and the research and production of pyridine and derivatives thereof are urgent for alleviating the domestic contradiction between supply and demand. The research and development of the process technology for synthesizing pyridine and derivatives thereof have wide market prospect and also have important significance for the development of the fine chemical industry in China.
Disclosure of Invention
The invention aims to provide a compound which can be used as a medical intermediate, namely (3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride, and a synthetic method thereof.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a compound, which is 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride, and the molecular structure of which is shown in formula 1:
the invention also provides a synthetic method of the compound, which takes 5-methoxypyridine-2, 3-dicarboxylic acid as a raw material to synthesize the compound through six-step reaction, and the synthetic route is as follows:
the synthesis method comprises the following steps:
s1, adding 5-methoxypyridine-2, 3-dicarboxylic acid into ethanol, dropwise adding concentrated sulfuric acid at room temperature, heating and refluxing, and reacting for 12 hours to obtain 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester;
s2, adding the 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester obtained in the step S1 into tetrahydrofuran, cooling to-5-20 ℃, and adding NaBH in batches4Adding CaCl in portions after 0.5h2Slowly heating to room temperature for reaction for 12h to obtain 2, 3-dihydroxymethyl-5-methoxypyridine;
s3, adding the 2, 3-dihydroxymethyl-5-methoxypyridine obtained in the step S2 into tetrahydrofuran, cooling to-10 ℃, adding triethylamine, adding methanesulfonic anhydride, and reacting at 0 ℃ for 1h to obtain 5-methoxypyridine-2, 3-dimethyl sulfonic acid methyl ester;
s4, adding the 5-methoxypyridine-2, 3-dimethyl sulfonic acid methyl ester obtained in the step S3 into tetrahydrofuran, adding benzylamine, heating up and refluxing, and reacting for 12 hours to obtain 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine;
s5, adding the 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine obtained in the step S4 into 1, 2-dichloroethane, mechanically stirring, dropwise adding ethyl chloroformate at room temperature, heating to reflux reaction after dropwise adding, and standing overnight to obtain ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate;
s6, adding the 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylic acid ethyl ester obtained in the step S5 into methanol, adding a KOH aqueous solution after the system is clear and transparent, heating to 90 ℃, reacting overnight, and reacting to obtain 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride.
Preferably, the reaction temperature of the step S1 is 55-70 ℃.
Preferably, the reaction temperature of the step S4 is 60-70 ℃.
Preferably, the reaction temperature of the step S5 is 75-90 ℃.
Preferably, the reaction temperature of the step S6 is 80-100 ℃.
The invention has the beneficial effects that: the method is simple, low in cost and high in efficiency, and provides a solid foundation for mass production and subsequent research of the compound materials.
Detailed description of the invention
The following detailed description will provide specific embodiments of the present invention. These embodiments are merely illustrative and not intended to limit the scope or the principles of the invention, which is defined by the claims and includes obvious modifications and variations based thereon.
Example 1
Synthesis of S1, dimethyl 5-methoxypyridine-2, 3-dicarboxylate:
in a 500mL four-necked flask, 23.6g of 5-methoxypyridine-2, 3-dicarboxylic acid was dissolved in 200mL of anhydrous methanol, 4.7g of concentrated sulfuric acid was added dropwise, and the temperature was raised to 65 ℃ after completion of the addition, followed by reaction for 12 hours. TLC monitors the reaction of raw materials completely, spin-dries the reaction solution, adds 300mL ethyl acetate, washes with saturated sodium thiosulfate (2x100mL) and saturated sodium carbonate (2x100mL) in turn, dries, spins, pulpes, filters to obtain 14g of 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester, the yield is 53%.
S2, synthesis of 2, 3-dihydroxymethyl-5-methoxypyridine:
13g of dimethyl 5-methoxypyridine-2, 3-dicarboxylate in a 500mL four-necked flask was dissolved in 320mL of absolute ethanol, cooled to 0 ℃ and added in 5 portions6.7g of NaBH4After 0.5h, 38g of CaCl were added in 5 portions2Naturally raising the temperature to room temperature for reaction for 12 h. TLC monitors that the raw materials are completely reacted, the reaction liquid is poured into a separating funnel, 100mL of saturated ammonium chloride solution and 500mL of water are sequentially added, dichloromethane (4x300mL) is used for extraction, organic phases are combined, dried, rotated, pulped and dried to obtain 7g of 2, 3-dihydroxymethyl-5-methoxypyridine with the yield of 70%.
S3, synthesis of methyl 5-methoxypyridine-2, 3-dimethylsulfonate:
in a 200mL reaction flask was added 7g of 2, 3-dimethylol-5-methoxypyridine dissolved in 100mL of tetrahydrofuran, 25g of triethylamine and 28g of methanesulfonic anhydride were added, and the mixture was reacted at 0 ℃ for 1 hour. TLC was used to monitor the completion of the reaction, the solvent was removed, 200mL of ethyl acetate was added, the mixture was washed with saturated sodium bicarbonate (2X100mL), and the dried organic phase was dried by evaporation to give 13.3g of methyl 5-methoxypyridine-2, 3-dimethylsulfonate in 100% yield and was directly used in the next step.
Synthesis of S4, 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine:
in a 500mL four-necked flask, 13.3g of methyl 5-methoxypyridine-2, 3-disulfonate was added to 150mL of tetrahydrofuran, and 17.5g of benzylamine was added, and the mixture was heated to 66 ℃ and reacted overnight. TLC monitors that the raw material reaction is complete, direct spin-drying is carried out, and the sample is stirred and passed through a column to obtain 5g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine with the yield of 51 percent.
Synthesis of S5, ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate:
5g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine was dissolved in 150mL of 1, 2-dichloroethane in a 250mL four-necked flask, and 2.5g of ethyl chloroformate was added dropwise and the reaction was allowed to proceed overnight at 84 ℃. TLC monitored complete reaction of starting material, spin-dried, and applied to the column with stirring to give 2g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate as a solid in 43% yield.
Synthesis of S6, 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride:
2g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate was dissolved in 50mL of anhydrous methanol in a 250mL four-necked flask, and 12.5g of KOH aqueous solution was added thereto, followed by warming to 90 ℃ and reacting overnight. TLC monitors the raw material reaction is complete, solvent is removed by rotation, dichloromethane (2x20 mL) is used for extraction, organic phases are combined, dried and dried by rotation to obtain a crude product, 20mL dioxane is added for dissolution, 2mL dioxane hydrochloride solution is added dropwise, stirring is carried out for 0.5H at room temperature, filtering is carried out, and a filter cake is dried to obtain 1.86g of 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride, wherein the yield is 96%.
Example 2
Synthesis of S1, dimethyl 5-methoxypyridine-2, 3-dicarboxylate:
in a 500mL four-necked flask, 23.6g of 5-methoxypyridine-2, 3-dicarboxylic acid was dissolved in 200mL of anhydrous methanol, 4.7g of concentrated sulfuric acid was added dropwise, and the temperature was raised to 55 ℃ after completion of the addition, and the reaction was carried out for 12 hours. TLC monitors that the raw materials react completely, spin-dries, adds 300mL ethyl acetate, washes with saturated sodium thiosulfate (2x100mL) and saturated sodium carbonate (2x100mL) in turn, dries, spins, pulpes and filters to obtain 13g of 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester, the yield is 50%.
S2, synthesis of 2, 3-dihydroxymethyl-5-methoxypyridine:
13g of dimethyl 5-methoxypyridine-2, 3-dicarboxylate in a 500mL four-necked flask was dissolved in 320mL of absolute ethanol, the temperature was reduced to-5 ℃ and 6.7g of NaBH was added in 5 portions4After 0.5h, 38g of CaCl were added in 5 portions2Naturally raising the temperature to room temperature for reaction for 12 h. TLC monitors the reaction of the raw materials completely, the reaction liquid is poured into a separating funnel, 100mL of saturated ammonium chloride solution and 500mL of water are sequentially added, dichloromethane (4x300mL) is used for extraction, organic phases are combined, dried, rotated, pulped and dried to obtain 7.1g of 2, 3-dihydroxymethyl-5-methoxypyridine with the yield of 71%.
S3, synthesis of methyl 5-methoxypyridine-2, 3-dimethylsulfonate:
in a 200mL reaction flask was added 7g of 2, 3-dimethylol-5-methoxypyridine dissolved in 100mL of tetrahydrofuran, and under mechanical stirring, 25g of triethylamine and 28g of methanesulfonic anhydride were added and reacted at 0 ℃ for 1 hour. TLC was used to monitor the completion of the reaction, the solvent was removed, 200mL of ethyl acetate was added, the mixture was washed with saturated sodium bicarbonate (2X100mL), and the dried organic phase was dried by evaporation to give 13.3g of methyl 5-methoxypyridine-2, 3-dimethylsulfonate in 100% yield and was directly used in the next step.
Synthesis of S4, 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine:
in a 500mL four-necked flask, 13.3g of methyl 5-methoxypyridine-2, 3-disulfonate was added to 150mL of tetrahydrofuran, and 17.5g of benzylamine was added, and the mixture was heated to 70 ℃ and reacted overnight. TLC monitors the reaction of the raw materials to be complete, spin-dries, and the sample is stirred and passed through the column to obtain 5.4g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine with the yield of 55%.
Synthesis of S5, ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate:
5.4g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine was dissolved in 150mL of 1, 2-dichloroethane in a 250mL four-necked flask, and 2.5g of ethyl chloroformate was slowly dropped at room temperature, and the mixture was reacted at 75 ℃ overnight. TLC monitored complete reaction of starting material, spin-dried, and applied to the column with stirring to give 2g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate in 41% yield.
Synthesis of S6, 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride:
2g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate was dissolved in 50mL of anhydrous methanol in a 150mL four-necked flask, and 12.5g of an aqueous solution of KOH was added thereto, followed by warming to 100 ℃ and reacting overnight. TLC monitors the raw material reaction is complete, solvent is removed by rotation, dichloromethane (2x20 mL) is used for extraction, organic phases are combined, dried and dried by rotation to obtain a crude product, 20mL dioxane is added for dissolution, 5mL dioxane hydrochloride solution is added dropwise, stirring is carried out for 0.5H at room temperature, filtering is carried out, and a filter cake is dried to obtain 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride 3.3g, wherein the yield is 95%.
Example 3
Synthesis of S1, dimethyl 5-methoxypyridine-2, 3-dicarboxylate:
in a 500mL four-necked flask, 23.6g of 5-methoxypyridine-2, 3-dicarboxylic acid was dissolved in 200mL of anhydrous methanol, 4.7g of concentrated sulfuric acid was added dropwise, and the temperature was raised to 70 ℃ after completion of the addition, and the reaction was carried out for 12 hours. TLC monitors the reaction of raw materials completely, spin-dries the reaction solution, adds 300mL ethyl acetate, washes with saturated sodium thiosulfate (2x100mL) and saturated sodium carbonate (2x100mL) in turn, dries, spins, pulpes and filters the organic phase to obtain 14.8g of 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester, the yield is 55%.
S2, synthesis of 2, 3-dihydroxymethyl-5-methoxypyridine:
13g of dimethyl 5-methoxypyridine-2, 3-dicarboxylate in a 500mL four-necked flask was dissolved in 320mL of absolute ethanol, the temperature was reduced to 10 ℃ and 6.7g of NaBH was added in 5 portions4After 0.5h, 38g of CaCl were added in 5 portions2Naturally raising the temperature to room temperature for reaction for 12 h. TLC monitors the reaction of the raw materials completely, the reaction liquid is poured into a separating funnel, 100mL of saturated ammonium chloride solution and 500mL of water are sequentially added, dichloromethane (4x300mL) is used for extraction, organic phases are combined, dried, rotated, pulped and dried to obtain 6.9g of 2, 3-dihydroxymethyl-5-methoxypyridine with the yield of 70%.
S3, synthesis of methyl 5-methoxypyridine-2, 3-dimethylsulfonate:
in a 200mL reaction flask was added 7g of 2, 3-dimethylol-5-methoxypyridine dissolved in 100mL of tetrahydrofuran, 25g of triethylamine and 28g of methanesulfonic anhydride were added, and the mixture was reacted at 0 ℃ for 1 hour. TLC monitors the reaction of the raw materials completely, the solvent is removed by rotation, 200mL ethyl acetate is added, saturated sodium bicarbonate (2x100mL) is used for washing, and the dried organic phase is dried by rotation to obtain 13.3g of the product methyl 5-methoxypyridine-2, 3-dimethylsulfonate, wherein the yield is calculated according to 100 percent and the product is directly put into the next step.
Synthesis of S4, 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine:
13.3g of 5-methoxypyridine-2, 3-dimethylsulfonate was added to a 300mL four-necked flask, and the mixture was dissolved in 150mL of tetrahydrofuran, and 17.5g of benzylamine was added thereto, and the mixture was heated to 60 ℃ to react overnight. TLC monitors the reaction of the raw materials to be complete, spin-dries, and the sample is stirred and passed through the column to obtain 6g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine with the yield of 61%.
Synthesis of S5, ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate:
6g of 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine was dissolved in 200mL of 1, 2-dichloroethane in a 500mL four-necked flask, and 3g of ethyl chloroformate was added dropwise and the mixture was reacted at 84 ℃ overnight. TLC monitored complete reaction of starting material, spin-dried, and applied to the column with stirring to give 3g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate as a solid in 50% yield.
Synthesis of S6, 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride:
in a 250mL four-necked flask, 3g of ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate was dissolved in 80mL of anhydrous methanol, 18g of an aqueous solution of KOH was added, and the mixture was heated to 80 ℃ to react overnight. TLC monitors the raw material reaction is complete, solvent is removed by rotation, dichloromethane (2x35mL) is used for extraction, organic phases are combined, dried and dried by rotation to obtain a crude product, 30mL dioxane is added for dissolution, 3mL dioxane hydrochloride solution is added dropwise, stirring is carried out for 0.5H at room temperature, filtering is carried out, and a filter cake is dried to obtain 2.3g of 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride, wherein the yield is 88%.
While there have been shown and described what are at present considered the fundamental principles and essential features of the invention and its advantages, it will be apparent to those skilled in the art that the invention is not limited to the details of the foregoing exemplary embodiments, but is capable of other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (4)
1. A synthetic method of a compound shown as a formula I is 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride, and is characterized in that 5-methoxypyridine-2, 3-dicarboxylic acid is used as a raw material to synthesize the 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride through a six-step reaction, and the synthetic route is as follows:
the synthesis method comprises the following steps:
s1, adding 5-methoxypyridine-2, 3-dicarboxylic acid into methanol, dropwise adding concentrated sulfuric acid at room temperature, heating and refluxing, and reacting for 12 hours to obtain 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester;
s2, adding the 5-methoxypyridine-2, 3-dicarboxylic acid dimethyl ester obtained in the step S1 into tetrahydrofuran, cooling to-5-20 ℃, and adding NaBH in batches4Adding CaCl in portions after 0.5h2Slowly heating to room temperature for reaction for 12h to obtain 2, 3-dihydroxymethyl-5-methoxypyridine;
s3, adding the 2, 3-dihydroxymethyl-5-methoxypyridine obtained in the step S2 into tetrahydrofuran, cooling to-10 ℃, adding triethylamine, adding methanesulfonic anhydride, and reacting at 0 ℃ for 1h to obtain 5-methoxypyridine-2, 3-dimethyl sulfonic acid methyl ester;
s4, adding the 5-methoxypyridine-2, 3-dimethyl sulfonic acid methyl ester obtained in the step S3 into tetrahydrofuran, adding benzylamine, heating up and refluxing, and reacting for 12 hours to obtain 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine;
s5, adding the 6-benzyl-3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine obtained in the step S4 into 1, 2-dichloroethane, mechanically stirring, dropwise adding ethyl chloroformate at room temperature, heating to reflux reaction after dropwise adding, and standing overnight to obtain ethyl 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylate;
s6, adding the 3-methoxy-5H-pyrrolo [3,4-b ] pyridine-6 (7H) -carboxylic acid ethyl ester obtained in the step S5 into methanol, adding a KOH aqueous solution after the system is clear and transparent, heating to 90 ℃ to react overnight, removing a solvent by rotation, extracting with dichloromethane, combining organic phases, drying by rotation to obtain a crude product, adding dioxane to dissolve, dropwise adding a dioxane solution, stirring at room temperature for 0.5H, filtering to obtain a filter cake, and drying the filter cake to obtain the 3-methoxy-6, 7-dihydro-5H-pyrrolo [3,4-b ] pyridine hydrochloride.
2. The method of synthesis of claim 1, wherein: the reaction temperature of the step S1 is 55-70 ℃.
3. The method of synthesis of claim 1, wherein: the reaction temperature of the step S4 is 60-70 ℃.
4. The method of synthesis of claim 1, wherein: the reaction temperature of the step S5 is 75-90 ℃.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101830898A (en) * | 2009-03-13 | 2010-09-15 | 上海普渡生化科技有限公司 | Preparation method of (S, S)-octahydro-6H-pyrrolo[3, 4-b] pyridine |
| CN101874019A (en) * | 2007-11-29 | 2010-10-27 | 弗·哈夫曼-拉罗切有限公司 | The method for preparing the method for isoindole derivatives and prepare their intermediate |
| WO2010131146A1 (en) * | 2009-05-12 | 2010-11-18 | Pfizer Limited | Cyclobutenedione derivatives |
| CN103260622A (en) * | 2010-12-20 | 2013-08-21 | 辉瑞大药厂 | Novel fused pyridine compounds as casein kinase inhibitors |
| CN103582482A (en) * | 2011-03-02 | 2014-02-12 | 利德探索中心有限公司 | Pharmaceutically active disubstituted triazine derivatives |
| CN105189480A (en) * | 2013-02-21 | 2015-12-23 | 多曼尼克斯公司 | Pyrimidine compounds useful in the treatment of diseases mediated by ikke and/or tbk1 mechanisms |
| CN109705116A (en) * | 2017-10-26 | 2019-05-03 | 赵明 | A kind of synthetic method of 6- benzyl-pyrrole simultaneously [3,4-b] pyridine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2100879A1 (en) * | 2008-03-13 | 2009-09-16 | 4Sc Ag | Novel N-substituted tetrahydroisoquinoline/isoindoline hydroxamic acid compounds |
| JP2018535993A (en) * | 2015-12-04 | 2018-12-06 | ヴィーブ ヘルスケア ユーケー リミテッド | Isoindoline derivatives |
-
2020
- 2020-08-03 CN CN202010765619.7A patent/CN111808102B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101874019A (en) * | 2007-11-29 | 2010-10-27 | 弗·哈夫曼-拉罗切有限公司 | The method for preparing the method for isoindole derivatives and prepare their intermediate |
| CN101830898A (en) * | 2009-03-13 | 2010-09-15 | 上海普渡生化科技有限公司 | Preparation method of (S, S)-octahydro-6H-pyrrolo[3, 4-b] pyridine |
| WO2010131146A1 (en) * | 2009-05-12 | 2010-11-18 | Pfizer Limited | Cyclobutenedione derivatives |
| CN103260622A (en) * | 2010-12-20 | 2013-08-21 | 辉瑞大药厂 | Novel fused pyridine compounds as casein kinase inhibitors |
| CN103582482A (en) * | 2011-03-02 | 2014-02-12 | 利德探索中心有限公司 | Pharmaceutically active disubstituted triazine derivatives |
| CN105189480A (en) * | 2013-02-21 | 2015-12-23 | 多曼尼克斯公司 | Pyrimidine compounds useful in the treatment of diseases mediated by ikke and/or tbk1 mechanisms |
| CN109705116A (en) * | 2017-10-26 | 2019-05-03 | 赵明 | A kind of synthetic method of 6- benzyl-pyrrole simultaneously [3,4-b] pyridine |
Non-Patent Citations (3)
| Title |
|---|
| A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold;Kostiantyn P. Melnykov等;《Amino Acids》;20181004;第51卷;第255-261页 * |
| A facile synthesis of 2,3-azaisoindoline;Subas M. Sakya等;《Tetrahedron Letters》;20100906;第51卷;第5859-5860页 * |
| Antibacterial activity of pyrrolopyridinesubstituted oxazolidinones: synthesis and in vitro SAR of various C-5 acetamide replacements;Paget，Steven D.等;《Bioorganic & Medicinal Chemistry Letters》;20060627;第16卷(第17期);第4537-4542页 * |
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