Category: 15963-46-9

Electric Literature of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick 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, Methyl 3-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Methyl 3-chlorocyclobutanecarboxylate

Step 1: Preparation of 3-((3-(Methoxycarbonyl)cyclobutyl)thio)benzoic Acid, Intermediate 20.0 A mixture of 3-mercaptobenzoic acid (2.1 g, 13.5 mmol), methyl 3-chlorocyclobutanecarboxylate (4.0 g, 26.9 mmol; purchased as a 9:1 diastereomeric mixture (favoring trans) from Synthonix, Inc.), and potassium carbonate (7.43 g, 53.8 mmol) in DMF was stirred at 50 C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The crude material was purified by MPLC using silica gel and eluting with a 0-40% EtOAc/EtOH (3:1) in heptane to provide 3-((3-(methoxycarbonyl)cyclobutyl)thio)benzoic acid (2.02 g) as white powder. 1H NMR (400 MHz, DMSO-d6) delta 12.91-13.22 (m, 1H), 7.74-7.77 (m, 2H), 7.44-7.49 (m, 2H), 3.96 (tt, J=7.77, 8.97 Hz, 1H), 3.56-3.61 (m, 3H), 3.11-3.23 (m, 1H), 2.67-2.73 (m, 2H), 2.10-2.21 (m, 2H). LCMS-ESI (POS.) m/z: 289.0 (M+Na)+.

The synthetic route of 15963-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 15963-46-9, These common heterocyclic compound, 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, 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 solution of 8-chloro-N-(4-chloro-2-hydroxyphenyl)-4-oxo-chromene-2-carboxamide (190 mg, 543 m mol), methyl 3-chlorocyclobutane-l-carboxylate (105 mg, 75 m L, 543 mmol) in DMF (5 mL) was added CS2CO3 (260 mg, 782 miho) at room temperature and the resulting mixture was then stirred at 90 C for 12 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to give methyl 3-(5-chloro-2-(8-chloro-4-oxo-chromene-2-carboxamido)phenoxy)cyclobutane- 1- carboxylate (200 mg, 79.8 %) as a yellow foam, which was used in next step directly without further purification. MS obsd. (ESL) [(M+H)+]: 462.1.

The synthetic route of 15963-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-(1-(pentan-3-yl)-1H-pyrazol-4-yl)-6-(1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrazine (0.100 g, 0.311 mmol) and methyl 3-chlorocyclobutanecarboxylate (0.0925 g, 0.622 mmol) in DMF (1.56 mE, 0.311 mmol) was added cesium carbonate (0.203 g, 0.622 mmol) and the reaction mixture was stirred at 80 C for 5 hours. The reaction mixture was cooled to ambient temperature, diluted with water (15 mE) and stirred for 10 minutes. The reaction mixture was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (50% EtOAc/hexanes) to afford two isomers. Faster eluting peak: trans-methyl 3-(4-(4-(1-(pentan- 3 -yl)- 1 H-pyrazol-4-yl)pyrazolo [1 ,5-ajpyrazin-6-yl)- I H-pyrazol- 1 -yl)cyclobutanecarboxylate(28 mg, 21% yield) as an off-white foam. Slower eluting peak: cis-methyl 3-(4-(4-(1-(pentan- 3-yl)-l H-pyrazol-4-yl)pyrazolo [1 ,5-a]pyrazin-6-yl)- 1 H-pyrazol- 1 -yl)cyclobutanecarboxylate(58mg, 43% yield) as a thick 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, Methyl 3-chlorocyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 3-chlorocyclobutanecarboxylate

Step 1: To a 3-neck flask that had been purged and maintained with an inert atmosphere of nitrogen, was placed a solution of phenol (111 g, 1.18 mol) in DMSO (2000 mL). To thissolution was added potassium tert-butoxide (240 g, 2.14 mol), and the mixture was heated to80C with vigorous stirring under an argon atmosphere for 15 minutes. To the above solution was added methyl 3-chlorocyclobutanecarboxylate (160 g, 1.08 mol) dropwise with stirring followed by tetrabutylammonium iodide (238 g, 0.646 mol). The reaction mixture was stirred for 1.5 h at 80C. The mixture was cooled to 10C, quenched with water (30 mL), and theaqueous layer was extracted with EtOAc (3 x 1000 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (1:40 EtOAc:petroleum ether) to afford methyl 3-phenoxycyclobutanecarboxylate as a solid.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FISCHER, Christian; BOGEN, Stephane, L.; CHILDERS, Matthew, L.; LLINAS, Francesc Xavier Fradera; ELLIS, J. Michael; ESPOSITE, Sara; HONG, Qingmei; HUANG, Chunhui; KIM, Alexander, J.; LAMPE, John, W.; MACHACEK, Michelle, R.; MCMASTERS, Daniel, R.; OTTE, Ryan, D.; PARKER, Dann, L., Jr.; REUTERSHAN, Michael; SCIAMMETTA, Nunzio; SHAO, Pengcheng, P.; SLOMAN, David, L.; UJJAINWALLA, Feroze; WHITE, Catherine; WU, Zhicai; YU, Yang; ZHAO, Kake; GIBEAU, Craig; BIFTU, Tesfaye; BIJU, Purakkattle; CHEN, Lei; CLOSE, Joshua; FULLER, Peter, H.; HUANG, Xianhai; PARK, Min, K.; SIMOV, Vladimir; WITTER, David, J.; ZHANG, Hongjun; (297 pag.)WO2016/89797; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 15963-46-9, 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. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thiol (0.1 g, 0.41 mmol), cesium carbonate (0.17 g, 0.51 mmol), and sodium iodide (0.006 g, 0.04 mmol) were dissolved in 2 mL DMSO. Methyl 3-chlorocyclobutanecarboxylate (0.09 g, 0.61 mmol, 0.08 mL) was added and the mixture was stirred at 100 C. for 40 hr. The reaction was diluted with EtOAc and H2O, and product was extracted with EtOAc (3*15 mL). The organic layers were combined, washed with brine (2*15 mL), and evaporated in vacuo. The oil was subjected to silica gel chromatography eluting with 15% EtOAc: 75% Hex. The diastereomers were separated and fractions containing products were concentrated. Trans: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.91 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.48-4.38 (m, 1H) 3.73 (s, 3H) 3.40 (tt, J=10.4, 5.7 Hz, 1H) 2.94 (tt, J=8.4, 5.8 Hz, 2H) 2.56 (dtd, J=13.3, 6.4, 2.4 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 174.87, 164.01, 163.34, 138.08, 133.74, 131.58, 131.19, 127.61, 121.39, 52.07, 37.62, 35.22, 32.73; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 8.02 min. cis: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.90 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.30 (p, J=8.6 Hz, 1H) 3.71 (s, 3H) 3.17 (p=8.9 Hz, 1H) 2.95-2.85 (m, 2H) 2.55 (qd, J=9.7, 2.9 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 173.80, 164.17, 163.30, 138.03, 133.72, 131.57, 131.16, 127.59, 121.39, 52.02, 35.45, 34.45, 33.77; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 7.89 min.

The chemical industry reduces the impact on the environment during synthesis Methyl 3-chlorocyclobutanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; Larsen, Scott D.; Neubig, Richard; Hutchings, Kim; Kahl, Dylan; Lisabeth, Erika Mathes; (56 pag.)US2019/308947; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics