Category: pyrazoles-derivatives

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. 81945-73-5, name is 1H-Pyrazol-1-ol, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 81945-73-5

1-Benzyloxy-lH-pyrazole; To a mixture of pyrazol-1-ol (1 g, 11.9 mmol) and /-Pr2NEt (2.02 mL, 11.9 mL) in DCM (15 mL) at 0 0C was added BnBr (4.09 mL, 23.8 mmol). The mixture was allowed to warm up to r.t. and stirred at this temperature for 22 h. The mixture was concentrated in vacuo to afford a yellow paste. The crude product was purified by flash chromatography (silica gel, hexanes/DCM/Et2O (100:0:0 to 80:10:10), Rf 0.23 in hexanes/DCM/Et2O (34:3:3)) to provide the title product as a yellow oil (1.17 g, 56%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 81945-73-5.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 84547-86-4, name is 4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid, 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 84547-86-4, name: 4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid

Example 39 4-{3-[(1S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-1-methyl-1H-pyrazole-3-carboxamide A mixture of 4-bromo-1-methyl-1H-pyrazole-3-carboxylic acid (20.0 mg, 0.0976 mmol), NH4Cl (52.2 mg, 0.976 mmol), TBTU (62.6 mg, 0.195 mmol), DIPEA (0.0340 mL, 0.195 mmol) and DMF (2 mL, 20 mmol) was stirred at rt for 10 min. The material was extracted with EtOAc, and washed with sat. NaHCO3 (3*) to remove carboxylic acid starting material. The organic layer was concentrated in vacuo. 3-[(S)-1-(2-Chloro-3-fluoro-6-methoxyphenyl)-ethyl]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (15.0 mg, 0.0348 mmol), (1,1’bis-(diphenylphosphino)-ferrocene) palladium dichloride (3.57 mg, 0.00488 mmol), K2CO3 (20.2 mg, 0.146 mmol) and 4:1 dioxane:H2O (1 mL, 10 mmol) were added, and the mixture was heated to 95 C. for 30 min. The solution was used directly for HPLC purification, and the fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): delta=1.80 (d, J=7.1 Hz, 3H), 3.70 (br. s., 3H), 3.96 (s, 3H), 5.14 (q, J=7.2 Hz, 1H), 6.88 (dd, J=9.2, 4.2 Hz, 1H), 7.05 (t, J=8.8 Hz, 1H), 7.30 (d, J=1.0 Hz, 1H), 7.66 (s, 1H), 7.72 (s, 1H), 8.22 (br. s., 1H). MS (ES+): m/z=428.11/430.12 (100/50) [MH+]. HPLC: tR=1.33 min (polar-3 min, UPLC-ACQUITY).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); 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 5334-40-7 as follows. name: 4-Nitro-1H-pyrazole-3-carboxylic acid

Synthesis of 123-A. To a solution of 4-nitro-1H-pyrazole-3-carboxylic acid (8.00 g, 50.1 mmol) in MeOH (160 mL) was added SOCl2 (11.92 g, 100.2 mmol) dropwise under ice bath. Then the solution was stirred at room temperature overnight. The solution was concentrated in vacuo to give 123-A (8.70 g, 84percent) as a white solid.

According to the analysis of related databases, 5334-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 10199-68-5, 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 10199-68-5 as follows.

(5)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methyl-3-(4-phenyl- lH-pyrazol-l- vDpropanamide (C2iHi7F3 (0721) (0722) [00328] To a solution of 4-phenyl-pyrazole (0.50 g, 0.003468 mol) in anhydrous THF (10 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil (0.35 g, 0.00867 mol). After addition, the resulting mixture was stirred for 3 h. (7?)- 3-Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (8, 1.22 g, 0.003468 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using ethyl acetate and hexanes (1 :2) as eluent to afford 0.90 g of the titled compound as white needles. (0723) [00329] Compound 1003 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.40 (s, 1H, NH), 8.46 (d, = 2.0 Hz, 1H, ArH), 8.24 (dd, = 8.4 Hz, J = 2.0 Hz, 1H, ArH), 8.09 (d, = 8.4 Hz, 1H, ArH), 8.05 (s, 1H, Pyrazole-H), 7.82 (s, 1H, Pyrazole-H), 7.52-7.45 (m, 2H, ArH), 7.35-7.31 (m, 2H, ArH), 7.20-7.16 (m, 1H, ArH), 6.33 (s, 1H, OH), 4.50 (d, = 14.0 Hz, 1H, CH), 4.30 (d, = 14.0 Hz, 1H, CH), 1.40 (s, 3H, CH3); Mass (ESI, Positive): 415.1455[M+H]+.

According to the analysis of related databases, 10199-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25016-12-0, 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0242] Bis(2-methoxyethyl)aminosulfurtrifluoride (3.71 ml, 20.14 mmol)was added to a stirred solution of l,3-dimethyl-lH-pyrazole-4-carbaldehyde (500 mg, 4.03 mmol) in DCM (6 ml) at 0 C. Then the mixture was stirred at room temperature for overnight. The reaction was quenched by NaHC03 solution (20 ml), extracted with dichloromethane (3 x lOmL). The combined organic fractions were washed with brine (3 x 10 ml), dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC reverse phase (C-8), eluting with (MeCN/H20=2/l), to give 4-(difluoromethyl)-l,3-dimethyl-lH- pyrazole as an oil. LC/MS = 147 [M+l].

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, 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUANG, Rongze; TING, Pauline; ALI, Amjad; WU, Heping; BERLIN, Michael; STAMFORD, Andrew; WANG, Hongwu; ZHOU, Gang; KIM, David; DENG, Qiaolin; LIM, Yeon-Hee; YU, Younong; (201 pag.)WO2016/81290; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 92933-47-6, These common heterocyclic compound, 92933-47-6, name is 5-Isopropyl-1H-pyrazole-3-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.

General procedure: To a solution of HATU (104 mg, 0.27 mmol) and 3-isopropylpyrazole-5-carboxylic acid (36 mg, 0.22 mmol) in DMF (14 mL) was then added diisopropylethylamine (0.055 mL, 0.31 mmol). The reaction solution was stirred at room temperature for 2 h. 2-(Benzylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carbonitrile (75 mg, 0.21 mmol) was added in one portion. The solution was then stirred at room temperature overnight. The reaction was diluted with methylene chloride and washed. The aqueous layer was extracted with methylene chloride twice, the combined organic phases were dried over anhydrous MgSO4. The resulting residue was purified by column chromatography on silica gel (EtOAc/hexane = 2:1) to give title compound as a white solid (33 mg, 37%).

Statistics shows that 5-Isopropyl-1H-pyrazole-3-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 92933-47-6.

Reference:
Article; Nam, Mina; Kim, TaeHun; Kwak, Jinsook; Seo, Seon Hee; Ko, Min Kyung; Lim, Eun Jeong; Min, Sun-Joon; Cho, Yong Seo; Keum, Gyochang; Baek, Du-Jong; Lee, Jiyoun; Pae, Ae Nim; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 245 – 258;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 112029-98-8,Some common heterocyclic compound, 112029-98-8, name is (1-Methyl-1H-pyrazol-4-yl)methanol, molecular formula is C5H8N2O, 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.

Step B 4-(methoxymethyl)-1-methyl-1,1-pyrazole To a suspension of sodium hydride (0.128 g, 3.21 mmol) in tetrahydrofuran (5 mL, 60 mmol) at 0° C. was added (1-methyl-1H-pyrazol-4-yl)methanol (0.300 g, 2.68 mmol) in tetrahydrofuran (2 mL, 20 mmol). The reaction was stirred at room temperature for 1 h, and then cooled down with ice bath. Methyl iodide (0.83 mL, 13 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with brine and extracted with EtOAc (3*). The combined organic phases were washed with water, brine, then dried over Na2SO4, and concentrated under reduced pressure to give 261 mg (77.2percent yield) of the desired product as colorless oil, which was directly used for the next reaction. LC/MS found: 127.2 (M+1)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-1H-pyrazol-4-yl)methanol, its application will become more common.

Reference:
Patent; Incyte Corporation; Huang, Taisheng; Feng, Hao; Kong, Lingquan; Wang, Anlai; Ye, Hai Fen; US2013/96144; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 49633-25-2,Some common heterocyclic compound, 49633-25-2, name is 3-Isopropylpyrazole, molecular formula is C6H10N2, 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 mixture of3-isopropyl-lH-pyrazole (3.74 g), 2- chloro-5-trifluoromethylpyridine (6.17 g) and N- methylpyrrolidone (18.7 ml) was addedNaOH (trademark: Tosoh pearl, 2.03 g) while stirring the mixture at room temperature. After reaction as it was for 9 hours, water (38 ml) and 6N hydrochloric acid (85 ml) were added, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane and then with toluene to give2- (3-isopropyl-lH-pyrazol-1-yl)-5- (trifluoromethyl) pyridine (6.94 g, yield 80%) as a colorless oil. H-NMR (CDC13)8 : 1.33 (6H, d, J=7.0 Hz), 3.0-3. 2(1H, m), 6.34(1H, d, J=2.5 Hz), 7.97(1H, dd, J=8.7, 2.1 Hz), 8.05(1H, d, J=8.7 Hz), 8.47(1H, d, J=2.5 Hz), 8.6-8. 7(1H, 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-Isopropylpyrazole, its application will become more common.

Reference:
Patent; TAKEDA CHEMICAL INDUSTRIES, LTD.; WO2003/99793; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, 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 37599-58-9, Recommanded Product: (1H-Pyrazol-3-yl)methanamine

To a solution of 4-chloro-7-(l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazol-5- yl)quinolin-2-amine (20 mg, 0.061 mmol) and (lH-pyrazol-3-yl)methanamine (59.1 mg, 0.608 mmol) in DMSO (0.5 mL) was added Hunig’s Base (0.032 mL, 0.182 mmol). The reaction was heated to 120 C overnight. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were concentrated, then dissolved in 0.4 mL DCM and 0.4 mL TFA. After 1 hour, the reaction was complete by LCMS. The reaction was concentrated and azeotroped with DCM. The residue was dissolved in DMF, filtered through a syringe filter, and the crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 200 mm x 19 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1%trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 0-minute hold at 0% B, 0-40% B over 20 minutes, then a 4-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: XBridge C18, 200 mm x 19 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: a 3- minute hold at 0% B, 0-32% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to give N4-((lH-pyrazol-3-yl)methyl)-7-(lH-pyrazol-5-yl)quinoline-2,4- diamine (4.6 mg, 24.7%). NMR (500 MHz, DMSO-de) delta 8.00 (br d, J=8.2 Hz, 1H),7.75 (s, 1H), 7.72 (br s, 1H), 7.58 (br s, 1H), 7.54 (br d, J=7.9 Hz, 1H), 7.43 (br s, 1H),6.76 (s, 1H), 6.62 – 6.41 (m, 1H), 6.20 (s, 1H), 5.76 (s, 1H), 4.42 (br d, J=5.2 Hz, 2H). LC RT: 0.99 min. M/Z= 306.18. (1550)

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; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, The chemical industry reduces the impact on the environment during synthesis 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, I believe this compound will play a more active role in future production and life.

To a stirred solution of 1-methyl-1H-pyrazol-3-amine 58 (5.0 g, 51.50 mmol) in Conc.HC1 (40 mL) at 0°C, sodium nitrite (5.30 g, 77 mmol) in water was added at 0°C and the mixture was stirred at RT for 30 mm. Copper (I) chloride was dissolved in concentrated hydrochloric acid (10 mL) and added to the above mixture drop-wise. The reaction was heated at 60°C, catalytic amount of Cu(I)Cl was added at 60°C (initiating the evolution of gas). Reaction mixture was stirred at 60°C for 30 mm. The mixture was then poured to chilled 50percent NaOH solution & stirred properly; aqueous was extracted with DCM. The organic layer was washed with brine solution, dried over anhydrous sodium sulfate, filtered and solvents evaporated to obtain a crude product (5.50 g, quantitative yield). 1HNMR (400 MHz, CDC13): oe 7.27 (d, 1H), 6.15 (d, 1H), 3.85 (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-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics