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. category: nitriles-buliding-blocks

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., name: 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,
Nitriles – Chemistry LibreTexts

Reference 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,
Nitriles – Chemistry LibreTexts

Reference of 20249-16-5, A common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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 suspension of sodium hydride (80 mg, 1 .998 mmol) in dry Tetrahydrofuran (10 mL) cooled to 0 C with an ice bath was added dropwise a solution of ethyl 2- (diethoxyphosphoryl)acetate (448 mg, 1 .998 mmol) in Tetrahydrofuran (10 mL). The bath was removed and the mixture was stirred for 1 h at rt. The mxiture was then re-cooled to 0 C with an ice bath and a solution of 3-oxocyclobutanecarbonitrile (190 mg, 1 .998 mmol) in Tetrahydrofuran (2 mL) was then was added dropwise. The resulted mixture was then stirred overnight at rt. Water (20 ml) and diethyl ether (50 ml) were added, the aqueous phase was extracted with diethyl ether (2×20 ml), the combined extracts were washed with water and brine, dired over anhydrous Na2S04 and concentrated to give the title compound ethyl 2-(3- cyanocyclobutylidene)acetate (200 mg, 1 .21 1 mmol, 60.6 % yield) as a clorless oil. m/z: [M + H]+ Calcd for C9H12NO2 166.2; Found 166.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 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.

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

Reference 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.

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.

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

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; LEE, Po-shun; (180 pag.)WO2017/40606; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 20249-16-5, 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. 20249-16-5 name is 3-Oxocyclobutanecarbonitrile, 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.

A solution of 3-oxocyclobutane-1-carbonitrile* (CAS: 20249-16-5, 14.5 g, 152 mmol) in THF (250 mL) was added to a mixture of (EtO)2P(O)CH2CN (31.1 g, 175 mmol), LiBr (19.9 g, 229 mmol) and TEA (30.9 g, 305 mmol) in THF (300 mL) at about 25 C. After about 16 hrs, the mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography to afford the title compound as a light yellow oil (16.01 g, 89%).1H NMR (400 MHz, CD3CN) delta: 5.38 (s, 1H), 3.30-3.43 (m, 2H), 3.16-3.30 (m, 3H).LCMS m/z=119.1 [MH]+

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

Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

A mixture of lithium (Z)-l-(5-bromo-2-methoxypyridin-3-yl)-2- (dimethoxvphosphoryl)ethenolate (2.0 g, 5.8 mmol) and 3-oxocyclobutanecarbonitrile (1.1 g, 12 mmol) in p-dioxane (6 ml) was heated at 1200C by Microwave in Ih. The mixture was cooled, taken up in H2O, extracted with EtOAc (3x), dried over MgSO4, concentrated to provide the title compound. MS (m+1): 307.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Oxocyclobutanecarbonitrile, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/147544; (2008); 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Oxocyclobutanecarbonitrile

Compound 10-2 (8.0g, 84.21mmol) was dissolved in DCM (80mL) at 0C, added DAST (27g, 0.168mol). The reaction mixture was stirred overnight at room temperature, and the end of the reaction was monitored by TLC (petroleum ether/ethyl acetate = 3: 1). Ice water was added to the reaction solution, extracted with DCM, washed with saturated brine, and then dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure and purified by column chromatography (petroleum ether/ethyl acetate = 150: 1-30:1) to give the crude Compound 10-3 (8.1g) as a brown oil.

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

Reference:
Patent; KBP Biosciences Co., Ltd.; ZHANG, Hui; DONG, Yanyan; EP2738156; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Safety of 3-Oxocyclobutanecarbonitrile

a solution of 3-oxocyclobutane-1-carbonitrile (3.9 g, 41.01 mmol, 1.00 eq.) and 2-methylpropane-2-sulfinamide (4.97 g, 41.01 mmol, 1.00 eq.) in tetrahydrofuran (100 mL) was placed in a 250- mL 3-necked round-bottom flask and stirred for 16 hours at 70C. After cooled to room temperature, NaBH4 (780 mg, 20.53 mmol, 0.50 eq.) was added in portions and stirred for 30 mm at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate and the organic layers combined. Theresulting mixture was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 7.5 g (9 1%) of N-(cis-3-cyanocyclobutyl)-2- methylpropane-2-sulfinamide as a yellow solid. LC-MS: (M+H) = 201.

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; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts