Day: July 20, 2021

Synthetic Route of 612511-81-6,Some common heterocyclic compound, 612511-81-6, name is (1-Methyl-1H-pyrazol-3-yl)methanamine, molecular formula is C5H9N3, 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 Oxirane intermediate (16.0 g, 52.56 mmol) in iPrOH (200 ml), was added (1-methyl-1 H-pyrazol-3-yl)methanamine (8.76 g, 78.84 mmol). The reaction mixture was stirred under 50°C for 16 h, after that RM was concentrated under reduced pressure and purified by silica column chromatography using 100percent ethyl acetate as eluent to give (8.8 g, 40 percent) as a thick liquid.

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-3-yl)methanamine, its application will become more common.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; SHAMLOO, Mehrdad; JAHANGIR, Alam; YI, Bitna; EVANS, Andrew Kelley; GREEN, Michael John; (178 pag.)WO2017/197324; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, 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 120068-79-3, Application In Synthesis of 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile

In a three-necked flask equipped with a dropping funnel, a stirrer and a thermometer was added lmol of 5-amino-3-cyano-1-(2,6-dichloro-4- (trifluoromethyl) phenyl) -pyrazole (II), 1.5piomicron1 sodium trifluoromethylsulfinate, 800ml of toluene and 0.08 mol (III) ionic liquid,After stirring for 5 min, the mixture was cooled to -2 C with stirring under ice-cooling. The mixture was stirred under stirringIn the above reactor, a solution of 1.2 mol of phosphorus trichloride in 80 ml of toluene was slowly added dropwise, stirred and heated to 50 C for 5 h,The reaction was quenched with ice water, extracted with methylene chloride, the organic phase was kept and washed once with saturated sodium bicarbonate, washed with brine. 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-1H-pyrazole-3-carbonitrile(0.965mol, ? 96% yield) (I),, the purity was 97.7%; further recrystallization was carried out using toluene, and the yield was 90%To give a purity of ? 99% (yield ? 94%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Dongguan City, Green Wheat Field Digital Technology Co.,Ltd; Liu, Lirong; (6 pag.)CN105541718; (2016); A;,
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

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

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

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

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

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

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

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