Month: May 2021

Reference of 288148-34-5, 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. 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 1mL of a solution containing arylsulfonyl chloride or arylacyl chloride or arylisocyanates ([Diversity reagent 13{1-8},13{9-10} or 13{11-12}, 0.40 mmol, 5 equiv) in CH2Cl2was added to the resin followed by addition of DIEA (0.88 mmol, 11 eq). Thereactors were shaken for 2 h at room temperature. The resin was drained andwashed with DMF (3 x 5 mL), MeOH (1 x 5 mL), and CH2Cl2(3 x 5 mL), and dried under low vacuum. The procedure described abovewas repeated.

The chemical industry reduces the impact on the environment during synthesis 1-Methyl-1H-pyrazole-4-sulfonyl chloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Canale, Vittorio; Kurczab, Rafa; Partyka, Anna; Sataa, Grzegorz; Ledna, Tomasz; Jastrzebska-Wiesek, Magdalena; Wesoowska, Anna; Bojarski, Andrzej J.; Zajdel, Pawel; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 334 – 346;,
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. 287922-71-8, name is 4-Bromo-1-methyl-1H-pyrazole-3-carbonitrile, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

a) 500 mg (2.69 mmol) 4-Bromo-1-methyl-1H-pyrazole-3-carbonitrile, 1.21 mg (5.00 muMol) Pd(OAc)2, 44.7 mg (0.08 mmol) dppf and 661 mg (8.06 mmol) NaOAc are added to 20 mL MeOH and stirred in an atmosphere of CO (p=10 bar) at 120 C. over night. Then the solvent is removed and the residue is purified by HPLC (MeOH/H2O/TFA).

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; Boehringer Ingelheim International GmbH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/100211; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35344-95-7, 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.

General procedure: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 °C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 percent MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70percent) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

The chemical industry reduces the impact on the environment during synthesis 1H-Pyrazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

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

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 176969-34-9

The compound of formula (III) was added to a 5% aqueous solution of sodium hydroxide, reacted at 60 C for 3 hours, and then hydrochloric acid was added to neutralize the pH to a weak acidity,(IV) (40 mmol) was refluxed with thionyl chloride (0.4 mol) for 4 hours, and the compound of formula (IV)Methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chloride in the presence of 10 mL of methylene chloride was added to a solution of the compound of formula (V) Of ammonia(VI) 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide was obtained by distilling off the reaction at room temperature for 4 hours at the end of the reaction. (VII) was added to oxalyl chloride (0.1 mol), stirred at room temperature for 1 hour and refluxed for 5 hours. After completion of the reaction, the compound of formula (VII) was distilled off under reduced pressure.

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Wang Han; Zhai Zhiwen; Shen Zhonghua; Tan Chengxia; Weng Jianquan; Wu Hongke; (10 pag.)CN107033081; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 27006-76-4, These common heterocyclic compound, 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, 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: All reactions were carried out in vials under nitrogen atmosphere. Step 1: A solution of compound 8 (100 mumol, 1.0 equiv) and compound 9 (150 mumol, 1.5 equiv) in DMF (0.1 M) was treated with K2CO3 (300 mumol, 3.0 equiv) and stirred at 110 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 10. The crude aldehyde 10 (100 mumol, 1.0 equiv) was dissolved in acetone:water (2:1, 0.1 M) and treated with KMnO4 (600 mumol, 6 equiv) and stirred at 30 C for 16 h (LCMS check). The reaction was filtered and the filtrate concentrated to afford 11. The crude acid 11 (100 mumol, 1.0 equiv) was treated with HATU (120 mumol, 1.20 equiv) followed by the crude amine (100 mumol, 1.0 equiv) and NEt3 (300 mumol, 3.0 equiv). The reaction was stirred at 30 C for 16 h (LCMS check). The reactions were concentrated and purified directly by reversed phase preparative HPLC using a C18 column and eluting with acetonitrile-water (0.225% formic acid or pH = 10 NH4OH) gradient. All compounds were deemed greater than 95% purity by LCMS and HPLC.

The synthetic route of 27006-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Londregan, Allyn T.; Piotrowski, David W.; Futatsugi, Kentaro; Warmus, Joseph S.; Boehm, Markus; Carpino, Philip A.; Chin, Janice E.; Janssen, Ann M.; Roush, Nicole S.; Buxton, Joanne; Hinchey, Terri; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1407 – 1411;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 29097-00-5, A common heterocyclic compound, 29097-00-5, name is Methyl 3-amino-1H-pyrazole-4-carboxylate, molecular formula is C5H7N3O2, 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: A solution of 5-aminopyrazole 5g (1 mmol) and ynone 7 (1 mmol) inMeOH (1 mL) was added dropwise to a mixture of AcOH (0.5 mL) andwater (10 mL) and the mixture was stirred at r.t. for 7 days. The productwas extracted by CH2Cl2 (3×25 mL) and the combined organic phaseswere dried over anhydrous Na2SO4, filtered, and the filtrate was evaporatedin vacuo. The residue was purified by CC (EtOAc/hexanes).Fractions containing the product were combined and evaporated invacuo to give 10.

The synthetic route of 29097-00-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Petek, Nejc; ?tefane, Bogdan; Novinec, Marko; Svete, Jurij; Bioorganic Chemistry; vol. 84; (2019); p. 226 – 238;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, 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. Product Details of 16034-46-1

General procedure: The DCC (1.2 equiv) was added to the solution of 1 (0.2 mmol), DMAP (0.2 equiv), and appropriate carboxylic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) at 0 C. The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (2 × 10 mL). Then, the CH2Cl2 solution was washed with 5% HCl (3 × 30 mL), saturated NaHCO3 (3 × 30 mL) and saturated NaCl (3 × 30 mL), respectively. Subsequently, the organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. At last, the residue was purified by column chromatography over the silica gel to yield the pure target compounds.

The synthetic route of 1-Methyl-1H-pyrazole-5-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Guo, Rui-Hua; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 2877 – 2888;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 0 C solution of tert-butyl 4,6- dihydropyrrolo[3 ,4-c]pyrazole-5 (2H)-carboxylate (100.00 mg, 0.48 mmol) was added lithium bis(trimethylsilyl)amide (1.00 mL, 1.00 mmol) in THF. The mixture was stirred at 0C for 30 mi 2,2-Dimethyloxirane ( 0.29 mL, 2.39 mmol) was added and the mixture was stirred at rt for 3 h and heated to 80 C for 2 h under microwave irradiation. The crude material was diluted with EtOAc, washed with brine (3 x 30 mL), and concentrated under reduced pressure to a yellow oil. The yellow oil was absorbed onto silica and purified (FCC, Si02, 30-70% EtOAc:hexanes) to afford a 1:1 mixture of the title compounds: tert-butyl 2-(2-hydroxy-2-methylpropyl)-4,6-dihydropyrrolo [3,4-c]pyrazole-5(2H)-carboxylate and tenbutyl 1 -(2-hydroxy-2-methylpropyl)-4,6-dihydropyrrolo [3 ,4-c]pyrazole-5 (1 H)-carboxylate (70 mg, 52%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, Jillian; BOOKSER, Brett; CHEN, Mi; CHUNG, DeMichael; GUPTA, Varsha; HUDSON, Andrew; KAPLAN, Alan; NA, James; RENICK, Joel; SANTORA, Vincent; WO2015/164520; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 37687-24-4, 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. 37687-24-4, name is Diethyl 3,5-pyrazoledicarboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of diethyl 1H-pyrazole-3,5-dicarboxylate (3.00 g, 14.1 mmol), 2-bromo-1-(8-fluoronaph- thalen-2-yl)ethanone (Intermediate 205A, 3.78 g, 14.1 mmol) and potassium carbonate (2.15 g, 15.6 mmol) in acetone (40 ml) was stirred at RT overnight. After filtering off the solids, the filtrate was evaporated and the residue partitioned between dichloromethane and water. The organic phase was washed with water and brine, then dried over sodium sulfate and concentrated. The crude product was purified by flash-chromatography on silica gel (80 g, eluent: 0-20% ethyl ace- tate in petroleum ether) to give the title compound (4.21 g, 70% of theory, 94% purity). LC/MS [Method 6]: Rt = 1.25 min; MS (ESIpos): m/z = 399 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): d [ppm] = 8.85 (s, 1H), 8.22 (d, 1H), 8.14-8.10 (m, 1H), 7.94 (d, 1H), 7.77-7.72 (m, 1H), 7.55-7.50 (m, 1H), 7.39 (s, 1H), 6.46 (s, 2H), 4.33 (q, 2H), 4.24 (q, 2H), 1.32 (t, 3H), 1.18 (t, 3H).

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, Diethyl 3,5-pyrazoledicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); 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. 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 1018446-95-1

0196-1 tert-Butyl 4-amino-1H-pyrazole-1-carboxylate (25 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5 mg), cesium carbonate (45 mg), and tris(dibenzylideneacetone)dipalladium(0) (5 mg) were added to a solution of N-(7-bromo-1,5-naphthyridin-2-yl)-5-cyclopentyl-N-((2-(trimethylsilyl)ethoxy)methyl)-1,3,4-thiadiazole-2-amine (40 mg) in 1,4-dioxane (1 mL), followed by stirring at 100 C. for 8 hours in a nitrogen atmosphere. 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (5 mg) and tris(dibenzylideneacetone)dipalladium(0) (5 mg) were added thereto, followed by stirring at 100 C. for 3 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added thereto. The organic layer was collected by separation, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate, NH silica), thereby obtaining tert-butyl 4-((6-((5-cyclopentyl-1,3,4-thiadiazol-2-yl)((2-(trimethylsilyl)ethoxy)methyl)amino)-1,5-naphthyridin-3-yl)amino)-1H-pyrazole-1-carboxylate (40 mg). MS m/z (M+H): 609.

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; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics