Category: 20249-16-5

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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 20249-16-5

Step 2. 3-Hydroxycyclobutane-l-carbonitrile. Sodium borohydride (597 mg, 15.8 mmol) was added in portions into a cold (0 C) mixture of 3-oxocyclobutane-l- carbonitrile (1.0 g, 10.52 mmol) and anhydrous methanol (10 mL). After the addition the mixture stirred for 30 minutes, and then it was carefully poured into ice water. The mixture was extracted with ethyl acetate and the organic extracts washed with water and brine and dried over anhydrous MsS04. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes: EtOAc 2/1 ratio) to afford 3- hydroxycyclobutane-l-carbonitrile, 8: 1 isomeric mixture, as oil (920 mg, 92% yield): XH NMR (500MHz, CDCh) delta ppm [4.62 (m), 4.26 (m), 1H], [3.06 (m), 2.75 (m), 2H], [5.65 (m), 2.33 (m), 2H], 2.6 (m, 1), 2.31 (m, 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Oxocyclobutanecarbonitrile

3,3-difluorocyclobutanecarbonitrile[1268] Example 125 A (8.21 g, 86 mmol) in dichloromethane (135 mL) was stirred at room temperature, cooled to <10 C, added DAST (1 1.41 mL, 86 mmol), warmed to room temperature, and stirred for 2 hours. The mixture was poured into saturated aqeuous NaHCC (200 mL) and partitioned. The aqueous phase was extracted with 2 x 50 mL dichloromethane. The combined organic phase was dried (Na2S04), filtered, and concentrated to give Example 125B (9.14 g, 78 mmol, 90 % yield) as a brown oil. XH NMR (400 MHz, CDC13) ? 3.06 - 2.91 (m, 5H). According to the analysis of related databases, 20249-16-5, the application of this compound in the production field has become more and more popular. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
Nitrile – Wikipedia,
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Electric Literature of 20249-16-5, These common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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.

Example 73.2-(6-Fluoro- 1 -methyl- 1 H-indazol-3 -yl)-5H-pyrrolo [2,3 -b]pyrazine-7-carboxylic acid [ 1 -(cis-3 – hydroxy-cyclobutyl)-ethyl]-amideStep 1cis-3-Hydroxy-cyclobutanecarbonitrile H3-Oxocyclobutanecarbonitrile was prepared according to Elend, D.; Fengas, D.; Fray, J. M. Synthetic Communications, 2005, 35, 657. To a solution of 3-oxocyclobutanecarbonitrile (600 mg, 6.31 mmol) in MeOH (25 mL) at 0C was slowly added sodium borohydride (263 mg, 6.94 mmol). The reaction mixture was stirred at 0C for 1 h then quenched with water and brine and extracted with EtOAc (3x). The combined organics were dried over MgSC^ and concentrated to afford 500 mg (82%) of cis-3 -hydro xy-cyclobutanecarbonitrile as a colorless oil. 1H NMR(CDCls, 300 MHz): ? (ppm) 4.26 (quin, J=7.5 Hz, 1H), 2.70 – 2.82 (m, 2H), 2.50 – 2.66 (m, 1H), 2.26 – 2.41 (m, 2H), 2.09 (br. s., 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Shaoqing; DE VICENTE FIDALGO, Javier; HAMILTON, Matthew Michael; HERMANN, Johannes Cornelius; KENNEDY-SMITH, Joshua; LI, Hongju; LOVEY, Allen John; LUCAS, Matthew C.; LUK, Kin-Chun Thomas; LYNCH, Stephen M.; O’YANG, Counde; PADILLA, Fernando; SCHOENFELD, Ryan Craig; SIDDURI, Achyutharao; SOTH, Michael; WANG, Ce; WOVKULICH, Peter Michael; ZHANG, Xiaohu; WO2013/30138; (2013); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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 20249-16-5, category: nitriles-buliding-blocks

Example 59A 3,3-Difluorocyclobutanecarbonitrile Under argon, 14.57 g (153.2 mmol) of 3-oxocyclobutanecarbonitrile from Example 58A were initially charged in 200 ml of absolute dichloromethane, 40.48 ml (306.4 mmol) of diethylaminosulphur trifluoride dissolved in 50 ml of dichloromethane were added at 0 C. and the mixture was stirred at RT overnight. A little at a time, the reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, cooled to 0 C., and stirred for 30 minutes. The organic phase was separated off and the aqueous phase was extracted with 200 ml of dichloromethane. The combined organic phases were twice washed with water, dried over sodium sulphate, filtered and concentrated. This gave 15.2 g (85% of theory) of the title compound. GC-MS (Method H): Rt=1.43 min MS (ESpos): m/z=98 (M-F)+

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-Oxocyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; VALOT, Gaelle; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; RAY, Nicholas Charles; BACHERA, Dominika; (71 pag.)US2017/50961; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, 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 20249-16-5, HPLC of Formula: C5H5NO

NaBH4 (2.4 g, 63 45 mmol, 0 50 eq.) was added slowly to a -70C solution of 3-oxocyclobutane-l-carbonitrile (12 g, 126.18 mmol, 1.00 eq., prepared according example 33, step 1) in THF (100 mL) and water (5 mL). The resulting solution was stirred for 1 hour at -70C in a liquid nitrogen bath. The reaction was then quenched by the addition of 50 mL of water/ice. The resulting solution was extracted with ethyl acetate (3×100 mL) and the organic layers combined. The resulting mixture was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give 8.13 g (66%) of 3-hydroxycyclobutane-l-carbonitrile as colorless oil.

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-Oxocyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

After cooling a solution of 3-oxocyclobutanecarbonitrile (32 g, 336 mmol) in methanol (330 mL) to 0 C.,NaBH4 (6.37 g, 168 mmol) was added in small portions. The mixture was stirred at 0 C. for 1 hour.The reaction mixture was quenched with saturated aqueous NaHCO 3 and extracted with ethyl acetate (800 mL).The organic layer was dried over Na2SO4, filtered,Concentrated. This procedure was repeated two more times on the same scale, combined for purification by silica gel chromatography, eluting with 10: 1 to 1: 1 petroleum ether: ethyl acetate to yield the product (30.3 g, 296 mmol, yield). 70%).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Nitrile – Wikipedia,
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Synthetic Route of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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.

[0467] Synthesis of 3-hydroxy-3-((trimethylsilyl)ethynyl)cyclobutanecarbonitrile (108B): At -78C, n-BuLi (1.6M in hexane, 3.8ml) was added dropwise to a stirred solution of trimethylsilylacetylene (0.99ml, 7.0mmol) in THF(4ml) over 3 minutes. The reaction was stirred for 55rnin at -78C. Compound 108A in 1ml THF was added. The reaction was stirred at -78C for 2 hours. The reaction was quenched with saturated aqueous NH4CI solution, extracted with EtOAc. The organic layer was dried with MgSC and concentrated. The resultant crude was purified by column chromatography on silica to afford compound 108B.

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BRIZGYS, Gediminas; CANALES, Eda; HALCOMB, Randall, L.; HU, Yunfeng, Eric; KATO, Darryl; LINK, John, O.; LIU, Qi; SAITO, Roland, D.; TSE, Winston, C.; ZHANG, Jennifer, R.; (253 pag.)WO2016/33243; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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. Quality Control of 3-Oxocyclobutanecarbonitrile

into a 500-mL round-bottom flask, was placed a solution of 3-oxocyclobutane-l-carbonitrile (4 g, 42.06 mmol, 1.00 eq.) tetra(propan-2-yloxy)titanium (14.16 g, 62.90 mmol, 1.50 eq.) and 2- methylpropane-2-sulfinamide (6.12 g, 50.49 mmol, 1.20 eq.) in tetrahydrofuran (200 mL). The resulting solution was stirred for 16 hours at 65C. The reaction was cooled to 25C. Then NaBH4 (3.2 g, 84.60 mmol, 2.00 eq.) was added. The mixture was stirred for 2 hours at 25C. The reaction was then quenched by the addition of 200 mL of water. The solids were filtered out and the resulting solution was extracted with ethyl acetate (2×200 mL) and the organic layers were combined. The resulting mixture was washed with brine (2×300 mL), dried over sodium sulfate and concentrated under vacuum. This resulted in 7.2 g (85%) of N-(3- cyanocyclobutyl)-2-methylpropane-2-sulfinamide as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20249-16-5, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (178 pag.)WO2016/115090; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

20249-16-5, 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

3,3-difluorocyclobutanecarbonitrile[1268] Example 125 A (8.21 g, 86 mmol) in dichloromethane (135 mL) was stirred at room temperature, cooled to <10 C, added DAST (1 1.41 mL, 86 mmol), warmed to room temperature, and stirred for 2 hours. The mixture was poured into saturated aqeuous NaHCC (200 mL) and partitioned. The aqueous phase was extracted with 2 x 50 mL dichloromethane. The combined organic phase was dried (Na2S04), filtered, and concentrated to give Example 125B (9.14 g, 78 mmol, 90 % yield) as a brown oil. XH NMR (400 MHz, CDC13) ? 3.06 - 2.91 (m, 5H). 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; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts