Tag: M.W:100-200

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

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

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 63680-90-0 as follows. Formula: C3H5Cl2N3

A 4-neck, 500-mL round bottom flask was charged with 3-chloro-1H-pyrazol-4-amine.HCl (15 g, 128 mmol), THF (50 mL), and water (50 mL). Sodium bicarbonate (32.2 g, 383 mmol) was added in portions to control off-gassing, and the mixture was cooled to 5 C. Acryloyl chloride (12.44 mL, 153 mmol) was added at <20 C. and the reaction was stirred for 2 h, after which the reaction was diluted with water (100 mL) and EtOAc (100 mL). The organic layer was concentrated to dryness to afford a white solid, which was suspended in MTBE (50 mL) and stirred for 2 h. The suspension was filtered and the solid was rinsed with MTBE (50 mL) to afford the desired product, N-(3-chloro-1H-pyrazol-4-yl)acrylamide (IIa), as a white solid after drying (14.8 g, 68% yield), mp: 182 C. (decomposition). 1H NMR (400 MHz, DMSO-d6) delta 12.96 (s, 1H), 9.77 (s, 1H), 8.10 (s. 1H), 6.58 (dd, J=17.0, 10.2 Hz, 1H), 6.23 (dd, J=17.0, 2.1 Hz, 1H), 5.73 (dd, 10.2, 2.1 Hz, 1H). 13C NMR (101 MHz, DMSO-d6) delta 162.69, 130.76, 130.14, 126.62, 123.60, 116.53. ESIMS: m/z 172.0 ([M+H]+). According to the analysis of related databases, 63680-90-0, the application of this compound in the production field has become more and more popular. Reference:
Patent; Dow AgroSciences LLC; Yang, Qiang; Lorsbach, Beth; Zhang, Yu; Walsh, Martin J.; Kister, Jeremy; (9 pag.)US2018/186752; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35691-93-1, 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. 35691-93-1, name is Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 8 1-Acetyl-azetidine-3-carboxylic Acid [(S)-3-[5-(3,5-dimethyl-1-pyrazin-2-yl-1H-pyrazole-4-carbonyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-1-(3-fluoro-phenyl)-propyl]-amide (III-25) 3,5-Dimethyl-1-pyrazin-2-yl-1H-pyrazole-4-carboxylic acid-To a solution of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid ethyl ester (1 g, 5.95 mmol) in DMF (20 mL) cooled to 0 C. was added portionwise NaH (60% in mineral oil, 171 mg, 7.13 mmol). After hydrogen evolution ceased, 2-chloro-pyrazine (0.64 mL, 7.13 mmol) was added and the reaction was stirred at 50 C. for 24 h. The reaction mixture was cooled to RT, partitioned between EtOAc and saturated NH4Cl. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified via SiO2 chromatography eluding with hexane/EtOAc to afford 0.64 g (44%) of 3,5-dimethyl-1-pyrazin-2-yl-1H -pyrazole-4-carboxylic acid ethyl ester.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,5-dimethyl-1H-pyrazole-4-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Lemoine, Remy; Melville, Chris Richard; Rotstein, David Mark; Wanner, Jutta; US2007/191335; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid

To a 0C solution of 1 ,5-dimethyl- lH-pyrazole-4-carboxylic acid (1.0 g, 7.14 mmol) in DCM/MeOH (7 mL each) was added 2M TMSCHN2 in hexane (4.28 mL, 8.56 mmol). The reaction mixture was stirred at 0C for 1 h, then was allowed to warm to RT and stirred at RT overnight, then was concentrated in vacuo. The crude product was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (900 mg, 5.84 mmol, 82 % yield). LCMS, [M + H]+ = 155.2.

The synthetic route of 31728-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; WANG, Ying; (140 pag.)WO2019/126085; (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. 151521-49-2, name is 4-Isopropyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Sodium (1.58 g, 68.7 mmol) was dissolved in EtOH (250 mL) and to this solution was added 4-isopropyl-lH-pyrazol-5-amine (3) (7.17 g, 57 mmol) and diethyl malonate (10.2 mL, 63 mmol). The solution was heated under reflux for 16 h, cooled to rt and concentrated in vacuo. The residue was dissolved in water (60 mL) and acidified to peta = 3 with 2 M HCl and the formed precipitate collected by filtration. The title compound ICEC0004 was obtained as an off-white solid (8.10 g, 35% over three steps). M.p. 242-2430C (ethanol).

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; EMORY UNIVERSITY; IMPERIAL COLLEGE OF SCIENCE AND TECHNOLOGY; JOGALEKAR, Ashutosh, S.; WO2008/151304; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 112758-40-4, These common heterocyclic compound, 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde, 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.

PREPARATION 461-(3-Chloro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde; To a solution of 3-methyl-pyrazole-4-carbaldehyde (0.5 g, 4.5 mmol) in dry dimethylformamide (15 mL) is added potassium carbonate (2.5 g, 18 mmol,) at room temperature. The reaction mixture is stirred at 40 C. for 30 min and then 1-fluoro-2-chloropyridine (0.77 g, 6 mmol,) is added. The reaction mixture is heated at 70 C. for 16 h. After completion, the reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture is purified by chromatography on silica gel eluting with hexane/ethyl acetate (75:25, 65:35) to yield 0.525 g (52%) of the title compound. MS (m/z): 222 (M+1).

The synthetic route of 112758-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; US2011/118251; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 151049-87-5, 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. 151049-87-5 name is 3-Bromo-1-methyl-1H-pyrazole, 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.

1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole A mixture of 3-bromo-1-methyl-1H-pyrazole (100 mg, 0.62 mmol), 1,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (500 mg, 1.52 mmol), K3PO4 (400 mg, 1.88 mmol) and Pd(dtbpf)Cl2 (41 mg, 0.063 mmol) in 1,4-dioxane (2.5 mL) and water (0.5 mL) was stirred at 120 C. for 1 h under microwave irradiation. The mixture was then concentrated in vacuo and the residue purified by Biotage column chromatography (SNAP 25 g column, CH2Cl2/EtOH 100/0->99/1) to give the title compound as a yellow resin (45 mg, 26%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-1-methyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3N3O4, 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. SDS of cas: 5334-40-7

A mixture of 4-nitro-3-pyrazolecarboxylic acid (4.98 g, 31.7 mmol), trans 4-aminocyclohexanol (3.65 g, 31.7 mmol), EDAC (6.68 g, 34.8 mmol) and HOBt (4.7 g, 34.8 mmol) in DMF (120 ml) was stirred at ambient temperature for 16 hours. The mixture was reduced in vacuo, the residue taken up in CH2CI2 and washed successively with 5percent citric acid, saturated aqueous sodium bicarbonate, water and brine. The product was found to be mainly in the citric acid wash, which was basified and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and evaporated to give a white solid, which was triturated with CHCI3 to give 1.95 g of 4-nitro-1H-pyrazole-3-carboxylic acid 4-hydroxy-cyclohexylamide. (LC/MS: Rt 1.62, [M+H]+255).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5334-40-7, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77424; (2006); A1;; ; Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77425; (2006); 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. 56984-32-8, name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 56984-32-8

Example 11; [Show Image] Compound 6 was reacted with various benzylalcohols to give Compounds A-21, A-22, A-23 and A-24 via Mitsunobu reaction.

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; Shionogi & Co., Ltd.; EP1953145; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics