Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 4027-57-0, name is Ethyl 5-methylpyrazole-3-carboxylate, 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 4027-57-0, Recommanded Product: 4027-57-0

A mixture of ethyl 5-methyl-1H-pyrazole-3-carboxylate (4.0 g, 25.95 mmol) and NBS (5.08 g, 28.54 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 16 h. The mixture was taken up in EtOAc (200 mL) and the organics were washed with saturated brine solution. The organics were then separated and dried (Na2SO4) before concentrated to dryness. The crude was then purified by flash column chromatography (PE/EA=3/2) to give ethyl 4-bromo-5-methyl-1H-pyrazole-3-carboxylate (4.8 g, 79% yield) as a white solid. LCMS (ESI): [M+H]+=234.9.

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, Ethyl 5-methylpyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 113808-86-9,Some common heterocyclic compound, 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid, molecular formula is C6H8N2O2, 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 of Examples 251-253; The piperazine Example 1 (220 mg), EDC (i.e., 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride) (245 mg), HOBT (i.e., 1-hydroxybenzotriazole) (172 mg), acid (108 mg), and JPr2NEt (206 mg) were taken up in CH3CN and stirred at 25C (18 h). The solution was partitioned15 between EtOAc and 1 N NaOH(aq.). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave a solid. The solid was triturated with Et2O. The white solid was collected and dried to give 125 mg (42 %) of Example 251.

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-Dimethylpyrazole-4-carboxylic Acid, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2006/60461; (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. 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, A new synthetic method of this compound is introduced below., Recommanded Product: 25700-12-3

Step 2: Preparation of 3-(4-nitro-pyrazol-1-yl)-pyridine 3-Pyrazol-1-yl-pyridine (2 g, 0.032 mol) was dissolved in concentrated H2SO4 (32 mL 0.598 mmol) and cooled at -5 C. using an ice bath. To the reaction mass, a 1:1 mixture of concentrated HNO3 (30 mL, 0.673 mmol) and concentrated H2SO4 (30 ml, 15 Vol.) was added dropwise over a period of 30 min. Cooling was discontinued and the reaction mixture was stirred at room temperature overnight. After the reaction was complete, the mixture was poured over crushed ice and neutralized with saturated NaHCO3, filtered, washed with water and dried to furnish the nitro pyrazole as pale yellow solid (1.8 g, 68%): 1H NMR (400 MHz, DMSO-d6) delta 9.03 (d, J=2.8 Hz, 1H); 8.70 (dd, J=4.8, 1.6 Hz, 1H), 8.69 (s, 1H), 8.33 (s, 1H), 8.11-8.08 (m, 1H), 7.51 (dd, J=8.4, 4.8 Hz, 1H); MS (m/z) 191 [M+1].

The synthetic route of 25700-12-3 has been constantly updated, and we look forward to future research findings.

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

Application of 113808-86-9, 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. 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 135 2-(((3R,4S)-1-(3,5-dimethyl-1H-pyrazole-4-carbonyl)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile To a solution of 2-(((3R,4S)-3-fluoropiperidin-4-yl)oxy)-5-(4-((4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)amino)-1,3,5-triazin-2-yl)benzonitrile (35 mgs, 0.07 mmol) in DMF (1.0 mL) was added 3,5-Dimethyl-1H-pyrazole-4-carboxylic acid (19 mgs, 0.13 mmol), HATU (50 mgs, 0.13 mmol) and TEA (0.02 mL, 0.13 mmol). The above reaction mixture was stirred at room temperature for 2 h, evaporated under reduced pressure and purified via preparative HPLC (5-65% acetonitrile in water, 0.1% trifluoroacteic acid buffer) to yield the title compound. LCMS-ESI+ (m/z): [M+H]+ calcd for C34H37FN10O3: 652.7. found: 653.3 1H NMR (400 MHz, DMSO-d6) delta 10.74 (brs, 1H), 10.24-10.09 (m, 1H), 8.75 (s, 1H), 8.57 (m, 2H), 7.67-7.43 (m, 3H), 7.06 (d, J=9.6 Hz, 2H), 5.26-5.01 (m, 3H), 4.76 (m, 4H), 4.44 (m, 1H), 4.27-3.61 (m, 5H), 3.59-3.40 (m, 2H), 3.10-2.88 (m, 4H), 2.50 (s, 6H), 2.02-1.97 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 3,5-Dimethylpyrazole-4-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Gilead Sciences, Inc.; Du, Zhimin; Guerrero, Juan A.; Kaplan, Joshua A.; Knox, JR., John E.; Lo, Jennifer R.; Mitchell, Scott A.; Naduthambi, Devan; Phillips, Barton W.; Venkataramani, Chandrasekar; Wang, Peiyuan; Watkins, William J.; Zhao, Zhongdong; (593 pag.)US2016/96827; (2016); 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 4331-28-6 as follows. SDS of cas: 4331-28-6

To a mixture of 2-benzyl-6-(methylcarbamoyl)isonicotinic acid (251.8 mg, 0.93 mmol) and HATU(565.5 mg, 1.49 mmol) was added 1H-pyrazol-4-amine hydrochloride (166.0 mg, 1.39 mmol) andDMF (4 mL). DIPEA (0.570 mL, 3.26 mmol) was added and the mixture was stirred at rt for 3.5 h.The mixture was concentrated under a stream of nitrogen and then diluted with acetonitrile to a totalvolume of 5 mL and directly purified by MDAP (5 x 1 mL injection; high pH) and the required fractions(fraction 1 from each run) were evaporated under a stream of nitrogen. The residues were eachredissolved in methanol ( 5 mL), combined into a tarred vial and the solvent evaporated under a stream of nitrogen to give a pale yellow solid – 6-benzyl-N2-methyl-N4-(1H-pyrazol-4-yl)pyridine-2,4- dicarboxamide (198.9 mg, 0.59 mmol, 64 % yield)LCMS (2 mm High pH): Rt = 0.85 mi [MH]+ = 336.1.1H NMR (400 MHz, DMSO-d6) O ppm 12.71 (br. 5., 1 H), 10.88 (s, 1 H), 8.78 (q, J=4.5 Hz, 1H), 8.40 (d, J=1.5 Hz, 1 H), 8.02 (br. 5., 1 H), 7.90 (d, J=1.5 Hz, 1 H), 7.70 (br. 5., 1 H), 7.36 – 7.41 (m, 2 H), 7.29 – 7.36 (m, 2 H), 7.19 – 7.26 (m, 1 H), 4.25 (s, 2 H), 2.88 (d, J=4.9 Hz, 3 H)

According to the analysis of related databases, 4331-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (N.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan, Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (0 pag.)WO2018/158210; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 113808-86-9, 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. 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3,5-dimethyl-1H-pyrazole-4-carboxylic acid (9.6 mg, 0.069 mmol, Maybridge), piperidin-4-yl-benzothiazole (15 mg, 0.069 mmol, Compound 2h, Step 2), Hunig?s base (24 tL, 0.137 mmol) and HATU (39 mg, 0.103 mmol) was stirred overnight at room temperature in DMF (343 .iL). The reaction was purified directly by prep HPLC to give a pale yellow solid after freeze drying from dioxane (11.5 mg, 50 % yield). LCMS (ESI) m/z 341.4 (M+1) retention time 3.8 mm. ?HNMR (300MHz, CD3OD) oe = 7.95 (m, 2H), 7.50 (m, 1H), 7.44-7.38 (m, 1H), 3.55-3.41 (m, 1H), 3.3 1-3.01 (m, 2H), 2.50 (m, 2H),2.30 (s, 6H), 2.26-2. 12 (m, 2H), 1.95-1.78 (m, 2H).

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, 3,5-Dimethylpyrazole-4-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HARTY, Ronald, N.; FREEDMAN, Bruce, D.; WROBEL, Jay, E.; REITZ, Allen, B.; LOUGHRAN, H., Marie; WO2015/153554; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

10250-59-6, name is Methyl 1,3-dimethyl-1H-pyrazole-5-carboxylate, 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. Application In Synthesis of Methyl 1,3-dimethyl-1H-pyrazole-5-carboxylate

c. Synthesis of 1 ,3-dimethyl-pyrazole-5-carboxylic acid; 3,delta-dimethyl-pyrazole-delta-carboxylic acid methylester (5.14 Kg) is added to an aqueous solution of 20% sodium hydroxide (10 L) at O0C. The reaction mixture is stirred at room temperature for 18 hours and cooled to O0C. Concentrated hydrochloric acid (4.2 L) is then added to the reaction mixture in over 7 hours. The resulting thick slurry is stirred at room temperature for 18 hours. The mixture is filtered, and the solids are washed with water (500 mL), and dried in a vacuum oven for 18 hours (700C and 26 mm Hg) to provide 3.8 Kg of 1 ,3- dimethyl-pyrazole-delta-carboxylic acid (81 % yield with a purity of >97 % by HPLC).

The synthetic route of 10250-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2006/48761; (2006); A2;,
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. 149978-43-8, name is 2-Methyl-5-trifluoromethyl-2H-pyrazol-3-ylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 149978-43-8

Hydrochloric acid in 1,4-dioxane (10.5 mL, 42.0 mmol, 4 mol/L) followed by 1,1′- thiocarbonyldiimidazole (4.38 g, 23.3 mmol) were added to a stirred solution of l-methyl-3- (trifluoromethyl)-lH-pyrazol-5-amine [149978-43-8] (3.49 g, 21.1 mmol) in DCM (63 mL) under nitrogen. The reaction mixture was stirred at rt for 4.5 h before being left without stirring for a further 15.5 h. The reaction mixture was filtered and the pale yellow solid was washed with DCM (2 x 40 mL). The filtrate and washings were concentrated in vacuo to give an orange liquid which was purified by flash column chromatography on silica (gradient elution with 0% to 15% EtOAc in isohexane) to afford the title compound (3.0430 g, 14.688 mmol, 70%) as a colourless liquid. To confirm the presence of the title compound, a few drops of isobutylamine were added to the LCMS sample of the product before analysis to give the thiourea, LCMS [M+H]+ 281.0, RT 1.336 minutes, purity 100% (Method 15).

According to the analysis of related databases, 149978-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 128694-63-3, The chemical industry reduces the impact on the environment during synthesis 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

Example 309 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide In the same manner as in Example 259 and using 1-methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid (160 mg, 0.80 mmol), tetrahydrofuran (5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (170 muL, 2.0 mmol), N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (200 mg, 0.62 mmol) and N,N-dimethylacetamide (7 mL) as starting materials, the title compound (240 mg, 76%) was obtained as a white solid. 1H-NMR (DMSO-d6, 300 MHz) delta 0.74-0.86 (4H, m), 1.86-1.97 (1H, m), 2.27 (3H, s), 4.15 (3H, s), 7.05 (1H, d, J=9.6 Hz), 7.13 (1H, dd, J=8.3, 2.6 Hz), 7.30 (1H, d, J=2.6 Hz), 7.37 (1H, d, J=8.3 Hz), 7.49 (1H, s), 7.94 (1H, s), 8.04 (1H, d, J=9.6 Hz), 10.13 (1H, s), 11.08 (1H, s).

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-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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. 39753-81-6, name is Ethyl 2-(4-nitro-1H-pyrazol-1-yl)acetate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 2-(4-nitro-1H-pyrazol-1-yl)acetate

Under hydrogen (1 atm), to a solution of compound 33-b (1.0 g, 5 mmol) in methanol (10 mL) was added 10% Pd-C (0.1 g). The mixture was stirred at 25 C. for 12 hours, and then filtrated, the filtrate was concentrated under reduced pressure to give compound 33-a (760 mg, yield: 90%), which was used directly for the next step without purification. LC-MS (ESI): m/z=170 [M+H]+.

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; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics