Category: 35344-95-7

Synthetic Route of 35344-95-7, The chemical industry reduces the impact on the environment during synthesis 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

To a stirred solution of tert-butyl 6-methylsulfonyloxy-2-azaspiro[3.3]heptane-2- carboxylate 23-2 (500 mg, 1.72 mmol) and lH-pyrazole-4-carbaldehyde 23-3 (164.89 mg, 1.72 mmol) inDMF (10 mL) was added cesium carbonate (1.12 g, 3.43 mmol) and the reaction mixture was stirred at 80C for 16 hours. The reaction mixture was diluted with cold water and EtOAc, and the layers were separated. The organic layer was washed with water, brine, dried over NaiiSCfi and concentrated under reduced pressure to afford crude which was purified by column chromatography to afford tert-butyl 6-(3-formylpyrazol-l-yl)-2-azaspiro[3.3]heptane-2- carboxylate 23-4 (420 mg, 1.44 mmol, 84.01% yield) as gummy solid. LC MS: ES+ 292.2.

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, 1H-Pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 lH-pyrazole-4-carbaldehyde (500 mg, 5.20 mmol) in DMF (20 mL) was added l-bromo-2-methoxyethane (713 mg, 5.2 mmol) and CS2CO3 (3.40 g, 10.4 mmol). After stirring at 60 C overnight, water (20 mL) was added to the mixture and the mixture was extracted with EtOAc (50 ml x 3). The organic phase was washed with brine, dried over Na2S04 and concentrated to yield intermediate 50 (520 mg, 65%> yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-Pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron Nathaniel; (161 pag.)WO2018/50684; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., name: 1H-Pyrazole-4-carbaldehyde

4-FORMYL-PYRAZOLE-1-CARBOXYLIC acid tert-butyl ester (56). To a solution of 55 (0.31 g, 3.26 mmol) in acetonitrile (30 ml) was added BOC anhydride (0.71 g, 3.26 mmol) followed by DMAP (0.02 g). After 30 minutes of stirring at room temperature, the solvent was evaporated, water and EtOAc were added. Organic layer was separated, washed with 0.5 N HCl (10 ml) and brine (15 ml), dried (NA2S04) and concentrated to give 0.41 g (76percent yield) of the desired product which was used in the next step to prepare di-Boc-protected 2 without purification.

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; IMCLONE SYSTEMS INCORPORATED; WO2005/813; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1H-Pyrazole-4-carbaldehyde

In this case, C3 was reacted with 1H-pyrazole-4-carbaldehyde and cesium carbonate to afford tert-butyl 2-(4-formyl-1H-pyrazol-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate. This material was treated with (diethylamino)sulfur trifluoride to provide the requisite tert-butyl 2-[4-(difluoromethyl)-1H-pyrazol-1-yl]-7-azaspiro[3.5]nonane-7-carboxylate.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 4-fluorobenzonitrile (2.49 g, 20.6 mmol) and 4-formylpyrazole (1.98 g, 20.6 mmo) in 50 mL of DMF at 0 0C was added 95percent sodium hydride (0.54 g, 22.7 mmol) under nitrogen. The mixture was heated to 60 0C for 6 hours and cooled to room temperature, Water was added carefully and the mixture was then extracted with ethyl acetate. The combined extracts were washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 4~(4-formyMH-pyrazol-l-yl)benzonitrile.

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, 1H-Pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; DI MARCO, Christina, Ng; WO2010/19391; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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 35344-95-7 as follows.

A solution of 1H-pyrazole-4-carbaldehyde (2.05 g, 21.4 mmoL) and hydroxylamine hydrochloride (1.63 g, 23.5 mmol) in MeOH (50 mL) was stirred at room temperature for 19 hrs. The reaction mixture was concentrated to give 1H-pyrazole-4-carbaldehyde oxime (3.3 g, crude) as a yellow solid.

According to the analysis of related databases, 35344-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives 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 35344-95-7, COA of Formula: C4H4N2O

1-isopropyl-1H-pyrazole-4-carbaldehyde To a solution of lH-pyrazole-4-carbaldehyde (2.0 g, 21 mmol) and 2-iodopropane (5.32 g, 31.5 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.83 g, 20.7 mmol) in one portion. The resulting mixture was stirred at room temperature for 2 hours, before being quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 0-50% EtO Ac/heptane to obtain 1- isopropylpyrazole-4-carbaldehyde (1.2 g, 42% yield). 1H NMR (400 MHz, CDC13) delta 9.86 (s, 1H), 7.97 (s, 2H), 4.54 (p, / = 6.7 Hz, 1H), 1.55 (d, / = 6.7 Hz, 6H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian K.; GEHLING, Victor S.; HARMANGE, Jean-Christophe; LAI, Tommy; LIANG, Jun; DRAGOVICH, Peter; ORTWINE, Dan; LABADIE, Sharada; ZHANG, Birong; KIEFER, Jim; WO2015/135094; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, belongs to pyrazoles-derivatives 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 35344-95-7, Computed Properties of C4H4N2O

1H-Pyrazole-4-carbaldehyde (6.00 g, 62.44 mmol) was stirred as a suspension in DCM (200 mL). Pyridine (7.58 mL, 93.66 mmol) was added at room temperature and the reaction was stirred for 10 min. 4-Methylbenzenesulfonyl chloride (11.90 g, 62.44 mmol) was added and the reaction was stirred at room temperature for 3 h (Monitored by TLC (KMnO4 visualisation, 100percent EtOAc) which shows new higher running spot and complete conversion after 3 h). The reaction allowed to stand at RT for 16 h. The reaction was diluted with DCM (100 mL) and washed with a saturated aqueous solution of NaHCO3 (100 mL), water (2 x 100 mL), passed through a phase separation cartridge and concentrated under reduced pressure. The resulting residue was purified by flash silica chromatography eluting with 100percent DCM. Product containing fractions were concentrated under reduced pressure to afford 1-(p-tolylsulfonyl)pyrazole-4-carbaldehyde (13.05 g, 84 percent) as a white solid. IR: 1691 (CO), 1373 (SO) , 1180 (SO), cm-1; 1H NMR (400 MHz, CDCl3) 2.45 (s, 3H), 7.38 (d, J = 8.5, 2H), 7.95 (d, J = 8.5, 2H), 8.10 (s, 1H), 8.61 (s, 1H), 9.92 (s, 1H); 13C NMR (400 MHz, CDCl3) 21.80, 125.29, 128.70, 130.35, 134.62, 143.49, 147.03, 183.26.; HRMS [M+H]+ measured 232.0465, C11H10N2O3S requires 232.0461.

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:
Article; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Formula: C4H4N2O

To a stirred solution of (l-phenylazetidin-3-yl) methanesuifonate (500 mg, 2.20 mmol) and lH-pyrazole-4- carbaidehyde (317 08 mg, 3.30 mmol) in DMF (10 mL) was added cesium carbonate (1.43 g, 4.40 mmol) anf the reaction mixture was heated to 80 C for 16 hours. After consumption of starting material, the reaction mass was diluted with water, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude was purified by combi-flash column chromatography (using 30% ethyl acetate in n-hexane) to afford l-(l-phenyl-azetidin-3-yl)-lH-pyrazole-4-carbaldehyde (300 mg, 1.23 mmol, 55 80% yield, 93% purity, 000) as light yellow solid. LCMS (ES+) = 227 8 | M I f )

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 35344-95-7.

Reference:
Patent; C4 THERAPEUTICS, INC.; VEITS, Gesine, Kerstin; HE, Minsheng; HENDERSON, James, A.; NASVESCHUK, Christopher, G.; PHILLIPS, Andrew, J.; GOOD, Andrew, Charles; (471 pag.)WO2019/191112; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35344-95-7,Some common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 stirred solution of 1Hpyrazole4carbaldehyde (1.00 g, 10.40 mmol) and 6bromo4methylnicotinonitrile (2.05 g, 10.40 mmol) in dioxane (15 mL) were added K2CO3 (4.31 g, 31.20 mmol). The resulting reaction mixture was degassed with nitrogen for 5 minutes then copper (I) iodide (0.59 g, 3.12 mmol) was added, followed by transN,N’dimethylcyclohexane1,2diamine (2.59 mL, 16.4 mmol). The resulting mixture was degassed again for 10 minutes and heated at 110 °C for 1 h under microwave irradiation. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2040percent EtOAc/ nhexane) to obtain Intermediate 6 (1.15 g, 52.10percent) as pale yellow solid. 1H NMR (300 MHz, DMSOd6) G^ppm 2.62 (s, 3 H), 8.10 (s, 1 H), 8.38 (s, 1 H), 8.95 (s, 1 H), 9.37 (s, 1 H), 9.98 (s, 1 H). LCMS (methodD), retention time 1.68 min, [M+H] 213.2.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics