Category: pyrazoles-derivatives

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. 78703-53-4, name is 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 1,3-Dimethyl-1H-pyrazole-4-carboxylic acid

General procedure: Pyrazole acid chlorides 6a-b were prepared by refluxing 4a-b in thionyl chloride for 8 h. Pyrazole acid chlorides 6a-b (12 mmol) in anhydrous tetrahydrofuran (THF; 30 mL) were slowly added to a solution of amine derivatives or 5-methylisoxazol-3-ol (10 mmol) and K2CO3 (1.38 g, 10 mmol) in anhydrous THF (30 mL) at a controlled temperature of 5 C. The reaction proceeded at room temperature until 6a-b was no longer tested by TLC. The reaction solution was then filtered and the solvent distilled. The residue was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and recrystallized to generate the target pyrazole carboxamides and isoxazolol pyrazole carboxylates (7aa-bk). The product yields ranged from 40% to 80%. All 20 compounds were novel, and the physical and spectral data for these compounds are listed below.

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; Sun, Jialong; Zhou, Yuanming; Molecules; vol. 20; 3; (2015); p. 4383 – 4394;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 50877-42-4,Some common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, molecular formula is C10H9IN2, 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 4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2-carbonyl]- 3,3-dimethyl-piperazin-2-one (70 mg, 0.160 mmol) in DMF (1.750 mL) were added 1- benzyl-4-iodo-pyrazole (68.18 mg, 0.240 mmol), CuI (15.23 mg, 0.080 mmol) and K3PO4 (67.93 mg, 0.320 mmol). The mixture was degassed for 10 min, then to it was added N,N’-dimethylethane-1,2-diamine (14 mg, 16.91 muL, 0.159 mmol). The mixture was allowed to stir overnight at 100C. The suspension was cooled down, water was added along with EtOAc. The phases were separated to afford a crude mixture of 1-(1- benzylpyrazol-4-yl)-4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2- carbonyl]-3,3-dimethyl-piperazin-2-one (95.0 mg, 100.0%)

The synthetic route of 50877-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 154471-65-5, 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. 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

2-methyl-5-trifluoromethyl-2H-pyrazole-3-boronic acid: 1-methyl-3-trifluoromethyl-1H-pyrazole (1.00 g, 6.66 mmol) was dissolved in THF (25 mL) in an oven-dried round bottom flask and cooled to-78 C in an acetone/dry ice bath. 2.5 M n-butyl lithium/hexane (3.196 ml, 7.99 mmol) was added drop wise to the stirred solution followed by drop wise addition of triisopropyl borate (5.01 g, 26.64 mmol). The mixture was warmed to room temperature and stirred for three hours. The reaction mixture was adjusted to pH 6 with IN HCl solution followed by the removal of THF under vacuum. The aqueous phase was extracted with EtOAc (3×100 ml). The combined organic phase was washed with brine and dried over anhydrous MgS0(sub>4, filtered and evaporated to give 2-methyl-5-trifluoromethyl-2H-pyrazole-3-boronic acid (1.12 g, 5.80 mmol, 87 % yield) as a white solid: LCMS m/z (%) = 195 (M+H, 100). 1H NMR (400 MHz, DMSO-d₆) delta: 8.37-8.40 (m, 2H), 7.57 (dd, J= 4.0 Hz, 1H), 4.06 (s, 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, 1-Methyl-3-(trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/12254; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-11-9, name is 1-Methyl-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 25016-11-9, COA of Formula: C5H6N2O

1-Methyl-1H-pyrazole-4-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (6.0 g, 0.04 mol) and 50 g of acetic acid (0.83 mol) were mixed at room temperature. Add 12.5 g of ammonia-containing molecular mass concentration of 25% ammonia water and 100 ml of water. heating to 90 C, the reaction is exothermic, maintaining the reaction temperature of 100 C, refluxing reaction for 1 hour (to 1-methyl-1H-pyrazole-4-carbaldehyde reaction is complete), The reaction solution was cooled to room temperature, poured into ice water and quenched and diluted. neutralize until the reaction solution is neutral, extract with ethyl acetate, and dry. After concentrating the product, it is distilled under reduced pressure and recrystallized.The product obtained was 10.2 g, the yield was 95%, and the purity was over 99%.

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; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 155600-99-0,Some common heterocyclic compound, 155600-99-0, name is 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, molecular formula is C4H3Br2N3O2, 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.

Production example 7 3-bromo-5-(2′-hydroxyethylamino)-1-methyl-4-nitropyrazole 3 g (10.5 mmoles) of 3,5-dibromo-1-methyl-4-nitropyrazole are heated in a solution of 30 ml ethanolamine in 30 ml ethanol for 15 hours at boiling temperature. The reaction mixture is then poured on 200 ml water, the separated product is filtered, washed with water (20 ml) and vacuum dried. Additional product crystallizes from the filtrate when cooled (5 C.). 2.25 g (81 percent of theory) of 3-bromo-5-(2′-hydroxyethyl)amino-1-methyl-4-nitropyrazole are obtained in the form of yellow crystals with a melting point of 150 C. 1 H-NMR (60 MHz, DMSO-d6): =7.38 (s; wide; 1H; –NH; exchangeable with D2 O), 4.98 (s; wide; 1H; –OH; exchangeable with D2 O), 3.82 (s; 3H; N–CH3) and 3.60 ppm (m; 4H; –NH –CH2 –CH2). MS (70 eV):m/e=266 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; Wella Aktiengesellschat; US5663366; (1997); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 41680-34-6, A common heterocyclic compound, 41680-34-6, name is 3-Amino-1H-pyrazole-4-carboxylic acid, molecular formula is C4H5N3O2, 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.

A mixture of 5-amino-i H-pyrazole-4-carboxylic acid (807 mg, 6.35 mmol) and methyl 2,4- dioxopentanoate (i.83 g, i2.7 mmol) in acetic acid (4.9 ml, 86 mmol) was heated for i hat iioC in a microwave reactor. Upon cooling to room temperature, the reaction mixture waspoured into water and the resulting precipitate was filtered off. The residue was washed with methanol to give the title compound (6i 5 mg, 85% purity) together with unknown impurities.[C-MS (Method i): Rt = 0.62 mm; MS (ESIpos): m/z = 236 [M+H]1H-NMR (400 MHz, DMSO-d6) 6 [ppm]: i.906 (2.ii), 2.666 (i6.00), 2.855 (i.3i), 2.857 (i.32), 3.962 (2.ii), 4.003 (i5.5i), 7.570 (5.55), 8.583 (5.25), 8.753 (0.73).

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1105039-93-7, A common heterocyclic compound, 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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.

According to Scheme 3 Step 1: A solution of 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylic acid (34.4 mmol, 8.00 g), oxalyl chloride (68.9 mmol, 5.92 mL) and a drop of DMF in DCM (80 mL) was stirred for 1 hour at room temperature. After evaporation, the crude product was dissolved in DCM (30 mL) and was added at 0 C. to a solution of N,O-dimethylhydroxylamine hydrochloride (103 mmol, 6.31 g) in DCM (100 mL) followed by Et3N (138 mmol, 19.2 mL). The reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with a saturated solution of Na2CO3 (300 mL) and the aqueous phase was extracted with DCM. The organic phase was dried over MgSO4, was filtered and was concentrated to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (33.8 mmol, 9.30 g, 98%) as a beige solid.LC (Zorbax SB-C18, 3.5 mum, 4.6×50 mm Column): RT=1.78 min; MS m/z ES+=276.

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; Bolea, Christelle; Calanire, Sylvain; US2010/144756; (2010); 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. 20583-33-9, name is 1-(1H-Pyrazol-3-yl)ethanone, This compound has unique chemical properties. The synthetic route is as follows., Formula: C5H6N2O

Example 18, Step B[00173] To a solution of compound 18b (31 g, 280 mmol) in CH3CN (500 mL) was added iodine (38 g, 150 mmol) and then eerie ammonium nitrate (164 g, 300 mmol) and the reaction mixture stirred for 24 hours at r.t. A cold solution of 5% aqueous NaHS03 was added to the reaction mixture and the mixture extracted with EtOAc (300 mL><3). The combined organic layers were dried over MgSO-t, filtered and concentrated in vacuo to give product 18c (65 g, 98%) which was used without further purification. According to the analysis of related databases, 20583-33-9, the application of this compound in the production field has become more and more popular. Reference:
Patent; MERCK SHARP & DOHME CORP.; ADDEX PHARMA SA; LIVERTON, Nigel, J.; BOLEA, Christelle; CELANIRE, Sylvain; LUO, Yunfu; WO2012/6760; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3524-32-1, name is 5-Amino-1,3-dimethylpyrazole, 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. Safety of 5-Amino-1,3-dimethylpyrazole

General procedure: 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol, 173 mg) and acetophenone (1.5 mmol, 180 mg), CuI (10 mol %, 19 mg) and FeCl3.6H2O (10 mol %, 27 mg) were added in DMSO (2 mL) at 120C in a round-bottom flask equipped with a magnetic stirring bar and a reflux condenser. After completion of the reaction the organic mixture was extracted with ethyl acetate (3×50 mL) and then washed with brine solution. The organic fraction was dried with anhydrous sodium sulphate and concentrated in rotavapor under vacuum. The product was purified by column chromatography using silica gel (100-200 mesh, ethyl acetate/hexane as eluent).

The synthetic route of 5-Amino-1,3-dimethylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rastogi, Gaurav K.; Saikia, B-Shriya; Pahari, Pallab; Deb, Mohit L.; Baruah, Pranjal K.; Tetrahedron Letters; vol. 60; 17; (2019); p. 1189 – 1192;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 16034-48-3,Some common heterocyclic compound, 16034-48-3, name is 1-Pyrazoleacetic Acid, molecular formula is C5H6N2O2, 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.

[0462] A solution of Example 1G and DIPEA (0.15 M and0.43 M in DMA, respectively, 257 f.LL, 0.04 mmol Example1 G (1.0 equivalent) and0.12 mmol DIPEA (3.0 equivalents)),HATU (0.2 M in DMA, 257 f.LL, 0.052 mmol, 1.3 equivalents),and 2-(1H-pyrazol-1-yl)acetic acid (0.40 Min DMA,121 f.LL, 0.048 mmol, 1.2 equivalents) were aspirated fromtheir respective source vials, mixed through a perfluoroalkoxymixing tube (0 2 mm inner diameter), and loaded intoan injection loop. The reaction segment was injected into theflow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mLinternal volume) set at 100 C., and passed through the reactorat 180 fJ.Lmin- 1 (10 minute residence time). Upon exiting thereactor, the reaction was loaded directly into an injection loopand purified by preparative HPLC on a Phenomenex LunaC8(2) 5 flill 100 A AXIA colunm (50 mmx21.2 mm) Agradient of acetonitrile (A) and 0.1% ammonium acetate inwater (B) was used, at a flow rate of30 mLmin (0-0.5 min 5%A, 0.5-6.5 min linear gradient 5-60% A, 6.5-7.0 min lineargradient 60-100%A, 7.0-8.9 min 100%A, 8.9-9.0minlineargradient 100-5%A, 9.0-10 min 5%A) to yield the title com-pound (7.33 mg, 39% yield). 1H NMR (400 MHz, DMSOd6D20)o7.76 (d, 1=2.3 Hz, lH), 7.60-7.45 (m, 4H), 7.37-7.28 (m, lH), 7.07-6.87 (m, 3H), 6.31 (t, 1=2.1 Hz, lH), 5.82 (s,lH), 5.00 (s, 2H), 3.93 (q, 1=6.9 Hz, 2H), 3.36 (s, 3H), 1.14 (t,1=6.9 Hz, 3H). MS (ESI) m/z 481.1 (M+W).

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

Reference:
Patent; Bogdan, Andrew; Kati, Warren M.; McDaniel, Keith F.; Park, Chang H.; Sheppard, George S.; Wang, Le; US2015/158873; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics