Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 53312-82-6, name is 4-Amino-2-bromobenzonitrile, 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 53312-82-6, Product Details of 53312-82-6

To a 40 mL vial with a stir bar are added 4-amino-2-bromobenzonitrile (637 mg, 3.23 mmol), maleic anhydride (317 mg, 3.23 mmol), and cyclohexanone (1.70 mL, 16.2 mmol). The reaction is heated to 150 C. for 16 hours then cooled to room temperature. The product is purified by gradient flash chromatography eluding with 0% to 10% MeOH in CH2Cl2 to provide [1-(3-bromo-4-cyanophenyl)-2-oxo-2,4,5,6,7,7a-hexahydro-1H-indol-3-yl]-acetic acid as a tan solid (456 mg, 38% yield) (LC/MS m/z=375 [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; Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas; US2008/76813; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5653-62-3, name is 2,3-Dimethoxybenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 2,3-Dimethoxybenzonitrile

2,3-Dimethoxybenzonitrile (2.0 g, 12.3 mmol), ZnBr2 (2.8 g, 12.3 mmol), and sodium azide (0.88 g, 13.5 mmol) were suspended in H2O (25 mL) and iPrOH (3 mL) and heated behind a blast shield at reflux for 24 hours. The mixture was allowed to cool to ambient temperature and diluted with EtOAc and 2N HCl. The aqueous phase was back extracted with EtOAc and the combined organic phases were dried over Na2SO4, filtered through a 1/4″ silica gel plug, and the filtrate was concentrated under reduced pressure. The residue was purified by trituration with diethyl ether to provide the title compound. MS (DClTNH3) m/z 207 (MH-H)+, m/z 181 (M+NH4-HN3)+.

The synthetic route of 5653-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2006/86229; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 868-54-2, 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. 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 10% aqueoussolution of KOH (11.20 ml, 20 mmol) and phenacyl bromide2-d (20 mmol) were added consecutively to a stirredsolution of malononitrile dimer 1 (1.32 g, 10 mmol) in DMF(20 ml). The mixture was stirred for 2 h at 20C and dilutedwith an equal volume of H2O. The formed precipitate wasfiltered off, washed with H2O, EtOH, and hexane.

The synthetic route of 2-Aminoprop-1-ene-1,1,3-tricarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dyachenko, Vladimir D.; Toropov, Alexey N.; Rusanov, Eduard B.; Chemistry of Heterocyclic Compounds; vol. 51; 1; (2015); p. 31 – 33; Khim. Geterotsikl. Soedin.; vol. 51; 1; (2015); p. 31 – 33,3;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 152775-45-6, 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 152775-45-6 as follows.

Example 58 2,4-dimethoxy-7-(4-methoxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one To a solution of 4,6-dimethoxy-2-methyl nicotinamide (2.0 g, 10.2 mmol) in THF (80 mL), n-butyl lithium (19.12 mL, 30.6 mmol, 1.6 M solution in hexane) was added slowly under nitrogen at -78 C. After completion of addition the mixture was stirred for 1 h at 0 C. Then cooled to -78 C. and a solution of 4-methoxy benzonitrile (1.65 g, 10.2 mmol) in THF (10 mL) was added quickly. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature and stirred for 16 h at room temperature. Saturated NH4Cl solution was added with cooling. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated to give crude product. The crude product was purified by chromatography using 50% ethyl acetate in hexane and then 2% methanol in ethyl acetate to give 2,4-dimethoxy-7-(4-methoxy-3,5-dimethylphenyl)-1,6-naphthyridin-5(6H)-one (410 mg, 12%), as a yellow solid. Selected data: MS (ES) m/z: 341.1; mp 262-263 C. (at decomposition).

According to the analysis of related databases, 152775-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter Ronald; US2013/281397; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6136-93-2, name is 2,2-Diethoxyacetonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C6H11NO2

To a solution of diethoxyacetonitrile (5 g, 38.75 mmol) in methyl alcohol (40 mL) was added sodium ethoxide (0.42 g, 7.75 mmol). The reaction was stirred for 3 h at room temperature. The resulting solution was concentrated under vacuum, then the residue was diluted with dichloromethane (100 mL) and washed with water (20 mL). The organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum to afford methyl 2,2-diethoxyethanimidate (4.8 g, crude) as a yellow oil. The crude product was directly used in the next step without purification. LCMS (ESI) [M+H]+ = 162.

The synthetic route of 6136-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LIANG, Jun; MALHOTRA, Sushant; MENDONCA, Rohan V.; RAJAPAKSA, Naomi; SIU, Michael; STIVALA, Craig; TELLIS, John C.; WEI, BinQing; CHAN, Bryan K.; DROBNICK, Joy Alison; GAZZARD, Lewis J.; HEFFRON, Timothy; JONES, Graham; LAINCHBURY, Michael; MADIN, Andrew; SEWARD, Eileen; CARTWRIGHT, Matthew W.; GANCIA, Emanuela; FAVOR, David; FONG, Kin-Chiu; GOOD, Andrew; HU, Yonghan; (298 pag.)WO2020/23560; (2020); A1;,
Nitrile – Wikipedia,
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Reference of 3441-01-8, These common heterocyclic compound, 3441-01-8, name is 3-Cyanobenzamide, 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.

To a vial equipp ed with a stir bar were added 2-(l-(5-bromopyridin-2- yl)cyclobutyl)-lH-benzo[d]imidazole (23.5 mg, 0.0720 mmol), cesium carbonate (70 mg, 0.22 mmol), 3-cyanobenzamide (10 mg, 0.070 mmol), (l S,2S)-Nl,N2-dimethylcyclohexane-l,2- diamine (2.0 mg, 0.014 mmol), and dioxane (358 muUpsilon . The vial was purged with nitrogen, and copper (I) iodide (1.36 mg, 7.16 muiotatauiotaomicron) was added. The vial was purged with nitrogen for 3 minutes, then the vial was sealed and heated to 110 °C for 16 h. After 16 h the mixture was diluted with DMSO, filtered, and purified by reversed phase HPLC, eluting with water (0.1 percentTF A)-ACN to afford the title compound as a TFA salt (Ex. 46). XH NMR (600 MHz,DMSO-c) delta 10.77 (s, 1H), 8.95 (s, 1H), 8.45 (s, 1H), 8.30 (dd, J = 13.1, 8.4 Hz, 2H), 8.14 (d, J = 7.6 Hz, 1H), 7.86 – 7.78 (m, 3H), 7.76 (d, J = 8.6 Hz, 1H), 7.59 – 7.54 (m, 2H), 3.25 – 2.80 (m, 4H), 2.21 – 2.08 (m, 2H). MS (EI) m/z 394 [M+H]+. Example 47: 3 -Chloro-N-(6-( 1 -(6-cvano- 1 H-benzo [dl imidazol-2-yl)cvclobuty l)pyridin-3 – vDbenzamide

Statistics shows that 3-Cyanobenzamide is playing an increasingly important role. we look forward to future research findings about 3441-01-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 110882-60-5, 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. 110882-60-5, name is 3-Fluoro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1To a solution of 3-fluoro-5-nitrobenzonitrile (1.0 g, 6.02 mmoL) in TFA (8 mL) was added water (1 mL) and cone, sulfuric acid (2 mL). The reaction mixture was heated to 70 C and stirred for 24 h. Then the reaction mixture was cooled to 0 C and liquid ammonia solution was added. The solidified solid was filtered through Celite (diatomaceous earth) and washed with water to obtain 3-fluoro-5-nitrobenzamide (0.400 g, 36%>) as an off white solid. Observed mass (M-l): 183.02.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Fluoro-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin, F.; DU, Bingfan; NGUYEN, Hanh, Nho; ZHENG, Xiao, Mei; WO2011/103196; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 10412-93-8, name is N-Benzyl-2-cyanoacetamide, 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 10412-93-8, Quality Control of N-Benzyl-2-cyanoacetamide

General procedure: To a stirred solution of cyanamide (2, 1.1 mmol) in ethanol (2 mL) were added 2-hydroxybenzaldehyde (1 mmol) and piperidine(catalytic amount), and the resulting mixture was stirred at room temperature for 12 h. The suspension was then filtered to give 4, which was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Benzyl-2-cyanoacetamide, and friends who are interested can also refer to it.

Reference:
Article; Endo, Satoshi; Hu, Dawei; Suyama, Miho; Matsunaga, Toshiyuki; Sugimoto, Kenji; Matsuya, Yuji; El-Kabbani, Ossama; Kuwata, Kazuo; Hara, Akira; Kitade, Yukio; Toyooka, Naoki; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6378 – 6384;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 555-21-5, name is 4-Nitrophenylacetonitrile, 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 555-21-5, Formula: C8H6N2O2

A mixture of (4-nitrorhohenyl)-acetonitrile (4.33 g5 27 mmol), NaOH (3.24 g, 81 mmol), iodomethane (5.5 mL, 88 mmol), and tetrabutylammonium iodide (0.56 g, 1.5 mmol) was stirred in water (35 mL) and dichloromethane (35 mL) for 24 hrs at about 25C, extracted with dichloromethane, dried (MgSO4), and concentrated. The residue was dissolved in diethyl ether, filtered through Celite, concentrated, re-filtered through Celite with dichloromethane, and concentrated. This product was dissolved in ethyl acetate, treated with SnCl2 (20 g, 106 mmol). The mixture was stirred overnight at 7O0C, concentrated, and partitioned between ethyl acetate and IN aqueous NaOH. The organic layer was isolated, EPO washed with brine, dried (Na2SO4), and concentrated to afford the title compound (3.69 g). 1H NMR (300 MHz, CDCl3) delta 7.24 (d, 2H), 6.68 (d, 2H), 1.68 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Nitrophenylacetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; WO2006/65646; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

20L three-necked flask by adding 5.94L water, 270mL thiophosgene, the temperature control in the 20 ~ 30C ,457 g of 4-amino-2- (trifluoromethyl) benzonitrile was added portionwise under stirring,After the addition, the reaction was continued for 1 h. The reaction was complete by TLC method, extracted with dichloromethane (1 L x 3)The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, added with petroleum ether beating,Through liquid nitrogen crystallization, filtration, drying, the product 500g, yield 89.3%.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai DingYa Pharmaceutical Chemicals Co.,Ltd; Ruan, Shiwen; Yan, Haiyan; Xia, Hongfei; Xu, LiPing; (6 pag.)CN104016924; (2016); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts