Tag: M.W=100-200

These common heterocyclic compound, 50670-64-9, name is 5-Amino-2-methylbenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C8H8N2

Add a solution of sodium nitrile (2.1 g, 31 mmol) in water (15 mL) drop wise at 5 C to a stirred solution of 5-amino-2-methylbenzonitrile (4.0 g, 31 mmol) in 33% sulfuric acid (45 mL) and keep the temperature below 5 C. In a separate flask, add concentrated sulfuric acid (30 mL) cautiously to a stirred solution of sodium sulfate (21.7 g, 153 mmol) in water (15 mL) and heat the mixture to reflux. Add the prepared diazonium solution to the re fluxing mixture in portions and continue refluxing for 2 hours. Cool the mixture slowly to room temperature and stir overnight. Extract the mixture with ethyl acetate (2 x 100 mL) and wash the combined organic extracts with water (2 x 150 mL) and 10% NaOH water solution (3 x 100 mL). Acidify the combined NaOH extracts with concentrated HC1 and then extract with ethyl acetate (2 x 200 mL). Dry the organic extracts over Na2S04 and concentrate under reduced pressure to give the title compound as a yellow solid (2.4 g, 60%): ES/MS (m/z) 134 (M+H), which is used directly without further purification.

The synthetic route of 5-Amino-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Kevin Kun-Chin; XIE, Yinong; WU, Liang; ZHOU, Guoqiang; WO2015/89800; (2015); A1;,
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Some common heterocyclic compound, 859855-53-1, name is 3-Amino-4-fluorobenzonitrile, molecular formula is C7H5FN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C7H5FN2

Intermediate 28: (4-Fluoro-3-(pyrrolidin-l-yl)phenyl)methanamineStep 1: 4-Fluoro-3-(pyrrolidin-l-yl)benzonitrile3-Amino-4-fluorobenzonitrile (0.5 g, 3.67 mmol), 1 ,4-dibromobutane (0.439 ml, 3.67 mmol), sodium carbonate (0.779 g, 7.35 mmol) and toluene (3 ml) were added into a microwave vial. The resulting mixture was heated by microwave irradiation at 140 C for 2 hours. 1 ,4-dibromobutane (0.5 ml, 4.18 mmol) was added and the reaction mixture was irradiated at 140 C and at 160 C until the reaction had clearly stopped. The reaction mixture was diluted with dichloromethane and washed twice with water. The organic phase was dried over Na2S04, filtered and evaporated. The crude product was purified by column chromatography. 0.221 g of the title compound was obtained. NMR (400 MHz, CDC13) delta ppm 1.96 – 2.00 (m, 4 H) 3.39 – 3.48 (m, 4 H) 6.84 (dd, 1 H) 6.89 – 6.94 (m, 1 H) 6.96 – 7.04 (m, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 859855-53-1, its application will become more common.

Reference:
Patent; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; PIETIKAeINEN, Pekka; ROSLUND, Mattias; VAeISAeNEN, Emilia; WOHLFAHRT, Gerd; WO2012/152983; (2012); A1;,
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Electric Literature of 19179-31-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 19179-31-8 name is 3,5-Dimethoxybenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Adding 0.02 equivalents of anhydrous copper sulfate and 4.0 equivalents of potassium t-butoxide to a 25 mL Schlenk reaction tube, drying in vacuum for 15 minutes, and sequentially adding 1,4-dioxane 1.5 mL and t-butanol 1 mL under argon atmosphere, 3,5-dimethoxybenzonitrile 5.0 equivalents,1 mmol of 1-(phenylthio)benzyl-2-iodobenzene was placed in the reaction tube after adding polytetrafluoroethylene stopper was placed into an oil bath of the reaction 100 C for 4 h. After the reaction is completed, the solvent is removed by filtration, and the solvent is separated by column chromatography. The eluent is petroleum ether/dichloromethane/ethyl acetate (v:v:v=20:10:1) to give a yellow liquid as 2-(3,5-dimethoxyphenyl)-3-(phenylthio)-1H-indole. The yield was 98%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; University of Science and Technology of China; Kang Yanbiao; Shan Xianghuan; (12 pag.)CN108863894; (2018); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-(3-Nitrophenyl)acetonitrile

To a solution of 3-nitro-phenyl-acetonitrile (3.20 g, 19.7 mmol) in MeOH(50 mL) was added Pd/C (10% wt, -50% H20, 0.32 g) and the mixture was placed under H2 (80 psi) and stirred for 2 days at 22 0C. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give crude product as a yellow oil. The residue was purified by silica gel chromatography (ISCO, elution with 0-10% ethyl acetate in hexanes) to give xix-1-1 (1.15 g, 44%): MS m/z = 133 (M-H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 621-50-1.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3215-64-3, Quality Control of 2-(2,6-Dichlorophenyl)acetonitrile

4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (l-2a) (3.1 g, 18 mmol) was dissolved in 40 rtiL anhydrous dimethylformamide and cooled in an ice/methanol bath (-10 C) for 15 minutes under an atmosphere of nitrogen. Sodium hydride (0.73 g, 18 mmol) divided into 5 portions was added over the course of 5 minutes keeping the reaction mixture cooled with stirring. After an additional 5 minutes, a solution of 2,6-dichlorobenzylacetonitrile (1-la) (4.9 g, 27 mmol) in 12 mL anhydrous dimethylformamide was added drop wise via syringe. The resulting mixture was stirred at -10 C for 30 minutes then allowed to warm to room temperature overnight after which time the reaction mixture was cooled in an ice bath and slowly quenched with 50 mL saturated NEUCl. After stirring for 20 minutes the product was extracted into DCM. The combined DCM extracts were dried over MgSCk, filtered, and concentrated under reduced pressure. The residue was re-dissolved in ethyl acetate and washed with brine. The organic layer was filtered through a sintered glass funnel and the filtrate was dried over sodium sulfate, filtered, and concentrated under reduced pressure to dryness. The residue was purified by silica gel chromatography eluting with ethyl acetate/dichloromethane to afford 708 mg (11%) 6-(2,6- dichlorophenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-amine (l-3a). LCMS (ESI):[M+H]? = 336.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,6-Dichlorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); A1;,
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Electric Literature of 115279-57-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (6.4 g, 23.6 mmol) and 2-(4-aminophenyl)-2-methylpropionitrile (5.6 g, 35 mmol) were dissolved in tert-butanol (200 mL), to the system added potassium carbonate (16.4 g, 119 mmol), and the reaction mixture was stirred under reflux for 2 h. After confirming a disappearance of the raw materials by a thin layer chromatography plate (ethyl acetate:petroleum ether=1:3), the reaction mixture was suction filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether to give 8.1 g of a pale yellow solid.

The synthetic route of 2-(4-Aminophenyl)-2-methylpropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Wu, Frank; Zhang, Yan; US2015/166539; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2032-34-0, name is 3,3-Diethoxypropanenitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2032-34-0, Quality Control of 3,3-Diethoxypropanenitrile

Step 1. l-cyclopropyl-lH-pyrazol-5-amine [0634] A 100-mL round-bottom flask was charged with 3,3-diethoxypropanenitrile (0.600 g, 4.19 mmol), cyclopropylhydrazine di-hydrochloride (0.610 g, 4.21 mmol) and ethanol (20 mL), and the resulting solution stirred for 18 h at 80 C. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10: 1, dichloromethane/methanol) to afford l-cyclopropyl-lH-pyrazol-5-amine (0.206 g, 36% ) as light yellow oil. MS (ESI, pos. ion) m/z 124[M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
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Reference of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a) 3-Bromo-6-fluoro-2-methylbenzonitrile To a cooled (0 C.) solution of 2-fluoro-6-methylbenzonitrile (2 g, 14.8 mmol) in concentrated sulfuric acid (40 mL) was added NBS (2.7 g, 15.6 mmol). The resulting residue was stirred at 0 C. for 3 hrs and poured into ice-water (400 mL). The resulting solution was extracted three times with EtOAc (80 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography to yield 3-bromo-6-fluoro-2-methylbenzonitrile.

The synthetic route of 198633-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Sui, Zhihua; Subasinghe, Nalin; US2014/275172; (2014); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 41171-91-9 as follows. Formula: C6H7NO

To the solution of 3-cyanocyclopentanone prepared above (91.6 g) in MeOH (1300 ml) was added NaBH4 (32.0 g) in portions while maintaining the temperature between 20- 30 C. After the addition was completed the mixture was stirred at rt for 30min. The mixture was evaporated and purification of the residue by column chromatography on silica gel (50 % petroleum ether/EtOAc) afforded 3-Hydroxy-cyclopentanecarbonitrile (62.0 g) as a colorless oil. T

According to the analysis of related databases, 41171-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BERGERON, Philippe; BODIL VAN NIEL, Monique; DRAGOVICH, Peter; HURLEY, Christopher; KULAGOWSKI, Janusz; LABADIE, Sharada; MCLEAN, Neville James; MENDONCA, Rohan; PULK, Rebecca; ZAK, Mark; WO2013/7765; (2013); A1;,
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Electric Literature of 3939-09-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3939-09-1, name is 2,4-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Benzyl alcohol (0.77 g, 7.2 mmol) was added to a stirred suspension of potassium tert-butoxide (0.97 g, 8.6 mg) in dioxane (15 ml) at room temperature. After 10 minutes of stirring at room temperature 2,4-difiuorobenzonitrile (1.00 g, 7.2 mmol) was added in one portion. After another 90 minutes water (10 ml) was added and the mixture extracted with diethyl ether (3×10 ml), the combined organic phases were dried using a phase separator and concentrated to solids. The crude material was purified by column (0491) chromatography using silicon dioxide gel, eluting with 25-50% dichloromethane in petroleum ether to afford 2-(benzyloxy)-4-fluorobenzonitrile as a white solid (1.33 g, 81%). (0492) [00317] A cold solution of borane (1.4 ml, 1 M in tetrahydrofuran) was added to 2- (benzyloxy)-4-fluorobenzonitrile (208 mg, 915 mutauetaomicron). After 15 hours of stirring at room temperature additional borane (1.4 ml, 1 M in tetrahydrofuran) was added. After another 19 hours of stirring additional borane (1.0 ml, 1 M in tetrahydrofuran) was added. After 3 hours the mixture was added to sodium hydroxide (5 ml, 1 M aqueous), extracted with ethyl acetate (3×5 ml), the combined organic phases were dried using a phase separator and concentrated afford [2-(benzyloxy)-4-fluorophenyl]methanamine as oil (260 mg, quantitative). This material was used without further purification. (0493) [00318] N-Methyl-4-piperidone (150 mg, 1.32 mmol) was added to a stirred solution of [2-(benzyloxy)-4-fluorophenyl]methanamine (204 mg, 882 mueta omicron) in ethanol (5 ml), after 5 minutes sodium triacetoxyborohydride (372 mg, 1.76 mmol) was added. After 6 hours the reaction mixture was concentrated, redissolved in dichloromethane (5 ml), washed with sodium hydroxide (5 ml, 1 M aqueous), the aqueous phase was extracted with additional dichloromethane (2×1 ml), the combined organic phases were dried using a phase separator, and concentrated to afford the desired intermediate as a yellow oil (253 mg, 87 %).

The synthetic route of 2,4-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACADIA PHARMACEUTICALS INC.; BURSTEIN, Ethan, S.; OLSSON, Roger; BORGSTROeM, Bjoern, Gustav; JANSSON, Karl, Erik; SKOeLD, Niklas, Patrik; VON WACHENFELDT, Henrik; WAHLSTROeM, Larisa, Yudina; (250 pag.)WO2019/40107; (2019); A1;,
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