Tag: M.W=0-100

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

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 288-13-1 as follows. Quality Control of 1H-Pyrazole

Step 1: Preparation of 3-pyrazol-1-yl-pyridine To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere. The reaction mass was refluxed for 24 hrs at 80 C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43%): 1H NMR (400 MHz, CDCl3) delta 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

According to the analysis of related databases, 288-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel I.; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank J.; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; (118 pag.)US2016/60245; (2016); 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

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. 67-51-6, name is 3,5-Dimethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H8N2

(1000mg, 10.40mmol) and KOH (1675mg, 10.40mmol) was dissolved in DMSO, and the resulting heterogeneous solution was stirred at 80 1.5h, then cooled to room temperature. Then, added over 15 minutes a solution of 6M DMSO (876mg, 15.61mmol), and the reaction mixture was stirred for 2.5 hours. TLC observation to monitor whether the reaction is complete. The reaction was dissolved in water, the aqueous phase with CHCl3 extraction. The combined organic layers were washed with 100ml of water, dried over anhydrous Na2SO4, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 20% ethyl acetate in petroleum ether. To give a yellow oil.

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 67-51-6.

Reference:
Patent; Southern Medical University; Cheng Kui; Xu Yao; (20 pag.)CN109867662; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, SDS of cas: 930-36-9

The N-methylpyrazole sulfonyl chloride was prepared by adding N- methylpyrazole to chilled (0C) chlorosulfonic acid. The reaction mixture was allowed to warm to room temperature and then heated to 100C overnight under a stream of N2. The reaction mixture was then cooled to room temperature and chilled to 0C. To this solution was added thionyl chloride (2.5 eq. ) and the reaction was stirred at room temperature for 30 min. , then warmed to 70C for two hours. The reaction was cooled to room temperature and then chilled in an ice bath. Water and ice were slowly added to the reaction mixture to precipitate a white solid which was collected by filtration. The desired sulfonyl chloride was washed with cold water and hexane.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methylpyrazole, and friends who are interested can also refer to it.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/97162; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 25222-43-9 as follows. COA of Formula: C4H6N2O

General procedure: To a solution of compound 6 (131 mg, 0.50 mmol) in DMF (2 mL) was added pyrazole (51 mg, 0.75 mmol), K2CO3 (138 mg, 1.00 mmol). The mixture was heated at 100 °C for 1 h. Reaction mixture was cooled, ice cold water (30 mL) was added and then extracted with EtOAc twice (30 mL × 2) and the combined organic layers were washed by saturated brine (30 mL). Then the organic layers were dried over Na2SO4, filtered and evaporated to afford the crude product used without further purification, To a solution of CF3COOH (1 mL) in CH2Cl2 (4 mL) was added the remaining solid (92 mg, 0.30 mmol). The mixture was at room temperature for 3 h, and then it was concentrated under reduced pressure to afford the crude product 19 used without further purification. To a solution of the product (99 mg, 0.30 mmol) in DMF (8 mL) was added 3-[(R)-1-(4-fluorophenyl)ethylaminocarbonyl]-5-[methyl (methylsulfonyl)amino]benzoic acid (106 mg, 0.27 mmol), EDCI (52 mg, 0.27 mmol), HOBt (37 mg, 0.27 mmol), DIPEA (99 muL, 0.60 mmol) was added and the mixture was allowed to react overnight at room temperature. Then the resulting mixture was diluted by 50 mL EtOAc and washed with dilute HCl aqueous solution (30 mL), saturated aqueous NaHCO3 (30 mL) and saturated brine (30 mL) sequentially. The organic layers were dried over Na2SO4 and evaporated to give the residue, which was purified by silica gel chromatography to afford 20 (149 mg, 91.3 percent).

According to the analysis of related databases, 25222-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jia; Zou, Yiquan; Xu, Lei; Chen, Wuyan; Zhu, Yiping; Chen, Tiantian; Fu, Yan; Li, Li; Ma, Lanping; Xiong, Bing; Wang, Xin; Li, Jian; He, Jianhua; Zhang, Haiyan; Xu, Yechun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 270 – 283;,
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

Synthetic Route of 1072-68-0, A common heterocyclic compound, 1072-68-0, name is 1,4-Dimethylpyrazole, molecular formula is C5H8N2, 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.

Sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.65 mmol) was suspended in 12 ml tetrahydrofuran. A solution of 4-methyl-1 H-pyrazole (0.60 g, 7.3 mmol) in 2 ml tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at room temperature. Methyl iodide (0.45 ml, 7.23 mmol) was added drop-wise and the mixture was stirred overnight forming a precipitate. The mixture was filtered and the solid was washed with a little tetrahydrofuran and the filtrates combined to give a crude solution of 1 ,4-dimethyl-1 H-pyrazole. The crude solution was cooled in an ice-bath under nitrogen and n-butyl lithium (1 .6 M in hexanes, 3.70 ml, 5.92 mmol) was added drop-wise with stirring over 15 min. After addition, the mixture was stirred at room temperature for 2 h. The mixture was then cooled to -78 C and a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (1 .49 g, 5.89 mmol) in 2 ml tetrahydrofuran was added over 1 min. The mixture was stirred overnight, warming to room temperature. The solution was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The organic extract was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified using the Isolera purification system (ethyl acetate-hexanes gradient, 0:100 rising to 100:0) to give 710 mg (2.03 mmol, 41 %) of the title compound as a white solid. Purity 96%. 1H NMR (300 MHz, DMSO-d6) delta ppm 8.13 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 8.2 Hz), 7.66 (dd, 1 H, J = 8.2, 2.3 Hz), 7.08 (s, 1 H), 6.51 (d, 1 H, J = 5.3 Hz), 5.93 (d, 1 H, J = 4.7 Hz), 3.83 (s, 3H), 1.42 (s, 3H). UPLC/MS (3 min) retention time 1 .72 min. LRMS: m/z 349, 351 (M+1 ).

The synthetic route of 1072-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; GONZALEZ RODRIGUEZ, Jacob; LOZOYA TORIBIO, Maria Estrella; MATASSA, Victor Giulio; MIR CEPEDA, Marta; ROBERTS, Richard Spurring; VIDAL JUAN, Bernat; WO2013/10881; (2013); 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

Electric Literature of 132712-71-1, A common heterocyclic compound, 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol, molecular formula is C4H6N2O, 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.

General procedure: To a neat solution containing 11H-indeno[1,2-b]quinoxalin-11-one (1 mmol), pyrazolone (1 mmol), and malononitrile (1 mmol), 10% mol of Na2CO3 in ethanol(10 mL) was added. The reaction mixture was heated at 70 8C for 12 h. After completion of the reaction as indicated by TLC, the precipitate was filtrated and washed with cold ethanol to afford the pure product 8. 4.5 6′-Amino-3′-methyl-1’H-spiro [indeno[1,2-b] quinoxaline-11, 4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile (8a) Light green powder (0.36 g, yield 93%). Mp 263-266 C. IR (KBr) (vmax/cm-1): 3450, 3274, 3250, 3112, 2976, 2191, 1637, 1607, 1465, 1401. 1H NMR (250 MHz, DMSO-d6): deltaH (ppm) 1.12 (3H, s, CH3), 7.45-8.13 (10H, m, H-Ar and NH2), 12.51 (1H, s, NH). C NMR (62 MHz, DMSO-d6): deltaC (ppm), 9.5 (CH3), 56.5 (C-Spiro), 96.8 (C-CN), 119.3 (CN), 121.4, 122.1, 126.2, 129.4, 129.6, 130.1, 130.8, 133.5, 135.5, 136.0, 141.8,142.5, 151.4, 153.3, 155.9, 162.9 (C-Ar and C-Pyrazole), 164.8 (C-NH2). Anal. calcd for C22H14N6O: C, 69.83; H, 3.73; N, 22.21. Found: C, 69.88; H, 3.72; N, 22.22.

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:
Article; Soleimani, Ebrahim; Hariri, Mina; Saei, Parisa; Comptes Rendus Chimie; vol. 16; 9; (2013); p. 773 – 777;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics