Tag: M.W:100-200

Related Products of 133228-21-4, 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. 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of N,N-dimethyl-1H-pyrazole-1-sulfonamide obtained in Step A (6.74 g) in tetrahydrofuran (75 mL) was added dropwise n-butyllithium hexane solution (1.3 M, 31.1 mL) over 15 min at -78C. The reaction mixture was stirred at -78C for 15 min, and a solution of 1,2-dibromo-1,1,2,2-tetrachloroethane (13.8 g) in tetrahydrofuran (25 mL) was added dropwise thereto over 10 min. The reaction mixture was stirred at -78C for 15 min, and then at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.03 g). 1H NMR (400 MHz, CDCl3) delta 3.06 (6H, s), 6.42 (1H, d, J = 1.6 Hz), 7.60 (1H, d, J = 1.6 Hz)

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, N,N-Dimethyl-1H-pyrazole-1-sulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

NaH (33.08 g (19.85 mol, 60 percent) was washed with n-hexane, then dry DMF (500 mL) was added drop wise under N2 atmosphere and the mixture was stirred well. A solution of 3- (trif luoromethyl)- 1 H-pyrazole (75 g, 0.55 mol) in DMF (125 mL) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzyl chloride (86.3 g, 0.55 mol) in DMF (125 mL) was added drop wise and the overall reaction mixture was allowed to stir for 12 h at room temperature. Progress of the reaction was monitored by TLC (10 percent ethyl acetate/hexane, Rf~0.4). On completion of the reaction, the reaction contents were poured into ice water (500 mL) and the product was extracted with ethyl acetate (2 Chi 400 mL). The ethyl acetate layer was washed with 2N HCI (2 x 200ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by CC with 10percent ethyl acetate/n-hexane to yield 1 -(4-methoxybenzyl)-3-(trifluoromethyl)-1 H- pyrazole as a brown colored liquid (98 g, 70 percent). 400 mL). The ethyl acetate layer was washed with 2N HCI (2 x 200ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by CC with 10percent ethyl acetate/n-hexane to yield 1 -(4-methoxybenzyl)-3-(trifluoromethyl)-1 H- pyrazole as a brown colored liquid (98 g, 70 percent).

The synthetic route of 3-(Trifluoromethyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68464; (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. 56984-32-8, name is Ethyl 5-chloro-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

The 1 – methyl -5 – chlorine pyrazole -4 – formic acid ethyl ester (300 mg, 1 . 59 mmol), phenol (300 mg, 3 . 19 mmol) dissolved in DMF, is added cesium carbonate (1.52, 4 . 66 mmol), microwave reactor 130 C reaction 30 minutes, the reaction is finished, to be reaction liquid cooling to room temperature, poured into water, extracted with ethyl acetate, the organic layer using saturated salt water washing, drying of the organic layer, dryness, passes through the rapid preparation column purification product 280 mg, yield is 72%.

The synthetic route of 56984-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Shen Jianhua; Leng Ying; Zou Qingan; Ning Mengmeng; (116 pag.)CN105164112; (2017); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 23170-45-8, These common heterocyclic compound, 23170-45-8, name is Methyl 3-methyl-1H-pyrazole-4-carboxylate, 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.

Synthesis of methyl l-benzyl-S-methyl-lH^yrazole-4-carboxylate. [00186] To a solution of methyl 3-methyl-lH-pyrazole-4-carboxylate (280 mg, 2 mmol) in N, N-dimethylformamide (30 mL) was added (bromomethyl)benzene (0.34 g, 2 mmol) and potassium carbonate (0.55 g, 4 mmol). The mixture was stirred at 20 C and stirred for 12 hours. The solvent was evaporated in vacuo and the residue was purified by CXTH (Column:Dsisol, 10muMu, CI 8, 250 mm*50 mm; Mobile: aeetonitrile(0.1% formic acidj-water (0.1% formic acid), acetonitrile from 30% to 70% in 80 minutes; oven; 20C; flow rate: 50 mL/minute, wavelength; 214 nm) to give crude methyl 1 -benzyl-5-meth.yl- lH-pyrazole-4-earboxylate (200 mg, 42%). LRMS (M + H+) m/z calcd. 230.1 1 ; found 230.

Statistics shows that Methyl 3-methyl-1H-pyrazole-4-carboxylate is playing an increasingly important role. we look forward to future research findings about 23170-45-8.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew, S.; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NAVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2013/120104; (2013); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 26621-44-3, 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. 26621-44-3 name is 3-Nitro-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.

[313] To a 0 C solution of 3-nitro-1H-pyrazole (250.0 g, 2.17 mol, 1.0 eq) in anhydrous DMF (2.5 L; 10.2 vol eq) under nitrogen was added NaH (95.42 g of 60 %w/w, 2.39 mol, 1.1 eq) in batches over 30 min while maintaining temperature below 8 C. The mixture was stirred for 1 h then 2,4-difluoropyridine (300 mL, 3.29 mol, 1.5 eq) was added, and the reaction was warmed to room temperature and stirred for approximately 16 hours (h). The reaction mixture was diluted with water (12.5 L) and stirred vigorously for 1 h. The off-white solid was collected by vacuum filtration. The solid was re-suspended in water (2 L) and filtered, and this step was repeated once further. The product was dried under vacuum, then suspended in heptane (4L), stirred 3 h at room temperature, and filtered. The solid was washed with two further portions of heptane (2 L each) and dried under vacuum to provide 2-fluoro- 4-(3-nitro-1H-pyrazol-1-yl)pyridine (426.3 g of 92% purity, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 9.01 (d, J = 2.8 Hz, 1H), 8.45 (d, J = 5.7 Hz, 1H), 7.95 (ddd, J = 5.7, 1.9, 1.2 Hz, 1H), 7.81 (t, J = 1.4 Hz, 1H), 7.46 (d, J = 2.8 Hz, 1H) ppm. ESI-MS m/z calc. 208.04, found 209.01 (M+1).

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARIFSON, Paul, S.; COME, Joh, H.; COURT, John, J.; GALE-DAY, Zachary; GU, Wenxin; JACKSON, Katrina, L.; MAGAVI, Sanjay, Shivayogi; NANTHAKUMAR, Suganthini, S.; RONKIN, Steven, Michael; SWETT, Rebecca, Jane; TANG, Qing; (383 pag.)WO2018/107056; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 158001-28-6, 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. 158001-28-6, name is 5-Amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation #26. 3-Bromo-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine A suspension of 5-amino-1-tert-butyl-1H-pyrazole-4-carbonitrile (8.67 g, 0.0528 mol) in formamide (100 mL) was heated at 180 C. for about 4 hours. The reaction mixture was cooled, poured into ice water (200 mL), and the product was extracted with ethyl acetate (4*80 mL). The combined organic layers were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was taken up in ether (35 mL) and the precipitate was filtered, washed with ether (50 mL), and dried under reduced pressure to afford 1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (3.22 g, 0.0169 mol) as a white solid; RP-HPLC (30% to 95% acetonitrile/0.01M aqueous ammonium acetate, buffered to pH 4.5, over 4.5 min at 0.8 mL/min; lambda=190-700 nm; Genesis C18, 120 A, 3 mum, 30*4.6 mm column) Rt 1.38 min.

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, 5-Amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 131797-35-8, A common heterocyclic compound, 131797-35-8, name is 5-Chloro-3-(trifluoromethyl)-1H-pyrazole, molecular formula is C4H2ClF3N2, 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.

To a solution of ethyl 2-[7-(chloromethyl)-2-methyl-5-oxo-5H-[l,3]thiazolo[3,2-a]pyrimidin- 3-yl]propanoate (2 g, 6.35 mmol) in acetonitrile (30 mL) was added 5-chloro-3-(trifluoromethyl)-lH- pyrazole (1.1 g, 6.45 mmol), potassium iodide (1.06 g, 6.39 mmol), and potassium carbonate (2.2 g, 15.9 mmol). The resulting mixture was stirred for 2 h at 90 C, cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (1/4) to afford ethyl 2-(7-[[5-chloro-3-(trifluoromethyl)-lH-pyrazol-l-yl]methyl]- 2-methyl-5-oxo-5H-[l,3]thiazolo[3,2-a]pyrimidin-3-yl)propanoate (2.9 g, crude) as a brown solid. LCMS (ESI): M+H+ = 449.0.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; YU, Jiang; WU, Guosheng; YUEN, Po-Wai; VILLEMURE, Elisia; SCHWARZ, Jacob; LY, Cuong; SELLERS, Benjamin; VOLGRAF, Matthew; WO2015/52226; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 10010-93-2,Some common heterocyclic compound, 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, molecular formula is C5H5F3N2, 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: In a Biotage tube, the relevant trifluoromethylpyrazole (1 mmol) and sodium hydroxide (0.2 g, 5 mmol) were stirred in ethanol/water 1:3 (1.2 mL). The tube was sealed and heated at 120 or 150 C, as mentioned in the text for 1 h in a microwave oven. The resulting suspension was dissolved in water; the aqueous phase was washed with dichloromethane twice and made acidic with 2 N hydrochloric acid. This was extracted with ethyl acetate twice; the organic layer was washed with brine, dried over magnesium sulfate, and concentrated to dryness to yield the corresponding acid as described below. CAUTION: the reaction conditions used lead to the release of fluorine ions that attack the glass tubes. Never recycle the reaction tubes as their resistance toward pressure and temperature may have been weakened in a process, which is releasing sodium fluoride.

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

Reference:
Article; Ermolenko, Mikhail S.; Guillou, Sandrine; Janin, Yves L.; Tetrahedron; vol. 69; 1; (2013); p. 257 – 263;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 360056-45-7,Some common heterocyclic compound, 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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 solution of 4-amino-1 H-pyrazole-3-carboxylic acid methyl ester (0.634 Kg, 4.49 mol, 1 wt) in 1 ,4-dioxane (8.90 L, 9 vol) under nitrogen was treated with triethylamine (0.761 L, 5.46 mol, 1.2 vol) followed by 2,6-dichlorobenzoyl chloride (0.710 L, 4.96 mol, 0.72 vol) such that the internal temperature was maintained in the range 20 to 25 0C. Residual 2,6- dichlorobenzoyl chloride was washed in with a line rinse of 1 ,4-dioxane (0.990 L, 1 vol) and the reaction mixture stirred at 18 to 25 C until complete (16 hours) by TLC analysis (eluent: ethyl acetate: heptanes 3:1 ; Rf amin80.25, Rf product 0.65). The reaction mixture was filtered, the filter-cake washed with 1 ,4-dioxane (2x 0.990 L, 2x 1 vol) and the combined filtrates (red) progressed to Stage 4 without further isolation.Triethylamine (1.42L, 10.20 MoI, 1.2 vol) was added to solution of 4-amino-1H-pyrazole-3- carboxylic acid methyl ester (1.184Kg, 8.39 MoI, 1.0 wt) in 1,4-dioxane (10.66L, 9.0 vol) at 15 to 25C under nitrogen. 2,6-Dichlorobenzoyl chloride (1.33L, 9.28 MoI, 1.12 vol) was charged at 15 to 250C followed by a line rinse of 1 ,4-dioxane (1.18L, 1.0 vol) and the reaction mixture stirred at 15 to 25C for 14 to 24 hours. Reaction completion was determined by 1H NMR analysis2. The reaction mixture was filtered, the filter-cake washed with 1 ,4-dioxane (2x 1.18L, 2x 1.0 vol) and the combined filtrates progressed to Stage 4 without further isolation.

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/1101; (2008); 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 934758-92-6 as follows. Product Details of 934758-92-6

Fuming nitric acid (14.00 ml, 329 mmol) was added at 0 ‘C over a period of 10 min to a solution of 5-chloro-1 H-pyrazole (10.0 g, 97.5 mmol) in acetic acid (14.0 ml, 245 mmol). The resulting mixture was stirred at 0 ‘C for 2 h, then acetic anhydride (33.0 ml, 349 mmol) was added and the reaction mixture was stirred at rt. Progress of the reaction was monitored by TLC and LCMS and when starting material was deemed completely consumed (after 4h), the reaction mixture was poured into ice-water (70 mL) and basified with Na2C03 (60 g) and extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with aqueous saturated sodium bicarbonate (100 mL) and brine (50 mL), dried over Na2S04 and concentrated. The afforded solid was washed with n-pentane which gave the title compound (7.0 g, 6.2%) as a solid. MS (ES+) 147.93 [M+H]+.

According to the analysis of related databases, 934758-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDIVIR AB; ALBERTELLA, Mark; OeBERG, Fredrik; (96 pag.)WO2018/141749; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics