Day: August 18, 2021

Related Products of 20154-03-4,Some common heterocyclic compound, 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, molecular formula is C4H3F3N2, 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 c: NaH (33.08 g (19.85, 60percent), 1.5 eq) was added to small quantity of n-hexane and stirred well for 10 min. N-hexane was decanted, dry dimethylformamide (500 mL) was added drop wise under N2 atmosphere and stirred well. A solution of step-b product (75 g, 0.55 mol) in dimethylformamide (125 mL) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzoyl chloride (86.3 g, 0.55 mol, 1 equivalent) in dimethylformamide (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 (10percent ethyl acetate in n-hexane). On completion of the reaction, reaction contents were poured into ice water (500 mL) and the product extracted with ethyl acetate (2?????400 mL). Then the contents were dried over sodium sulfate and concentrated under reduced pressure to yield the required product as a brown colored liquid (125 g, 88percent).

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

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)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 368870-03-5, SDS of cas: 368870-03-5

Method 2: General procedure for the preparation of examples 19-21 and 29-31 via urea formation with N,N’-carbonyldiimidazole.The corresponding primary amine (33.7 mg, 0.19 mmol) was dissolved in DMF (0.5 mL) and N,N’-carbonyldiimidazole (31.5 mg, 0.19 mmol) was added. The mixture was stirred for 20 min at room temperature a then the secondary amine (50 mg, 0.19 mmol) was added and the mixture was stirred at 8O0C for 16 h. The product urea was obtained by preparative HPLC purification. l-r3-(2,6-dichlorophenyl)-5-methyl-l,2-oxazol-4-yll-l-methyl-3-r(4-pyrazol-l- ylphenvDmethyllureaThe titel compound was prepared by general method 2 using intermediate 11 and the commercially available (4-pyrazol-l-ylphenyl)methanamine. 1H NMR (400 MHz, CDCl3) delta (ppm) 7.91 (d, 1 H), 7.73 (d, 1 H), 7.57 – 7.62 (m, 2 H), 7.37 (br. s., 3 H), 7.26 (s, 2 H), 6.47 (s, 1 H), 5.01 (t, 1 H), 4.34 (d, 2 H), 3.13 (s, 3 H), 2.46 (s, 3 H); MS (ESI) m/z 456 [M+H].

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, (4-(1H-Pyrazol-1-yl)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/10784; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7119-95-1, name is 1-Nitropyrazole, 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 7119-95-1, Computed Properties of C3H3N3O2

Concentrated sulphuric acid (80 ml) was added dropwise to a stirred sample of 1-nitropyrazole (20.3 g) that was cooled in an ice-bath. The resultant mixture was stirred for 16 hours and allowed to warm to ambient temperature. The mixture was poured onto ice and stirred for 20 minutes. The resultant solid was isolated and washed with water. The filtrate was neutralised by the addition of potassium carbonate and extracted with diethyl ether. The recovered solid was added to the diethyl ether solution and the resultant solution was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-80° C.) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. There was thus obtained 4-nitropyrazole (16 g); 1H NMR: (DMSOd6+CF3CO2H) 8.57 (s, 2H).

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; Jung, Frederic Henri; Morgentin, Remy Robert; Ple, Patrick; US2009/76075; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4149-06-8, A common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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: The mixture of alpha,beta-unsaturated ketone 1, or 4 (1.0 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one 2 (1.0 mmol), p-TSAxH2O (0.3mmol), MeCN (4mL), H2O (4mL) was put in a reaction flask under 80 C about 1-3 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be precipitated out at same time. Then, it was filtered, washed thoroughly with MeCN. The products were recrystallized from DMF.

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Shuangshuang; Wang, Zhansheng; Li, Xiuling; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 72; 38; (2016); p. 5754 – 5761;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-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 138786-86-4, name: Methyl 4-nitro-1H-pyrazole-3-carboxylate

Reference Example 39 Methyl 4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate To a solution (275 mL) of methyl 4-nitro-1H-pyrazole-3-carboxylate obtained in Reference Example 1 (27.4 g, 160 mmol) and p-toluenesulfonic acid monohydrate (3.04 g, 16 mmol) in chloroform, 2,3-dihydropyran (19.0 mL, 330 mmol) was added at 0 C., and the mixture was warmed to room temperature, and stirred for 3 hr. The reaction mixture was washed with saturated aqueous sodium hydrogencarbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 2:1) to give the title compound (34.8 g, yield 85%) as pale-yellow oily substance. 1H-NMR (CDCl3): delta 1.62-1.77 (3H, m), 1.83-2.04 (2H, m), 2.15-2.27 (1H, m), 3.68-3.76 (1H, m), 3.99 (3H, s), 4.03-4.13 (1H, m), 5.43 (1H, dd, J=2.7 Hz, 9.1 Hz), 8.38 (1H, s).

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

Reference:
Patent; Tsukamoto, Tetsuya; Yamamoto, Takeshi; Tokunoh, Ryosuke; Kawamoto, Tomohiro; Okura, Masahiro; Kori, Masakumi; Murase, Katsuhito; US2009/156582; (2009); 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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Methyl-4-nitro-1H-pyrazole

General procedure: To a 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

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 3994-50-1.

Reference:
Article; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51985-95-6, name is Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O3, 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. COA of Formula: C6H8N2O3

Example 134; (S, E)-Methyl 4-(6-(l-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acrylamido)-2-(5- methoxy-1-methyl-1H-pyrazol-3-yl)ethyl)-3-oxo-2>3-dihydropyridazin-4- yl)phenylcarbamate; 134 A. methyl 5 -methoxy-1 -methyl- 1H-pyrazole-3-carboxylate: To a cooled solution (0 °C) of methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate (1.60 g, 10.25 mmol) and K2CO3 (2.124 g, 15.37 mmol) in DMF (10 mL) was added dropwise MeI (0.703 mL, 11.27 mmol). The reaction mixture was stirred under argon at rt for 5 days. The reaction mixture was diluted with EtOAc, washed with H2O (1 x 15 mL), saturated NaHCO3 (1 x 15 mL) and brine (1 x 15 mL). The organic phase was dried over MgSO^ filtered an Purification by normal phase chromatography gave 134A (1.20 g, 7.05 mmol, 68.8 percent yield) as a white solid. LC- MS (ESI) m/z: 171.2(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51985-95-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/114677; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 34605-66-8, These common heterocyclic compound, 34605-66-8, name is 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole, 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.

At -78 , 3- (2,5-dimethyl -1H- pyrrol-1-yl) -1-methyl -1H- pyrazole (708.5mg, 4.04mmol) in THF (8mL)Was added dropwise a solution of n-BuLi (2.4M in tetrahydrofuran, 2.5mL, 6.0mmol). The reaction system was stirred for 0.5 hours maintaining -78 , then0 moved after two hours while stirring. Acetone was added to the system (362.1mg, 6.24mmol), the resulting mixture was stirred at room temperature for 3Hours, then water (20 mL) to quench the reaction, and (50mL × 3) and extracted with ethyl acetate. The combined organic phases with saturated brine (50mL of), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc / PE (v / v) = 1/5) of pureOf the title compound as a yellow oil (353.0mg, yield 37.4%).

The synthetic route of 34605-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

2-bromoethoxy- xit y Id i met y I si I ane (CAS [86864-60-0]) (2.4 mL; 1 1 .4 mmol ) was added to a solution of 1 H-pyrazo le-4-carbaldehyde (CAS [35344-95-7] ) (910 mg; 9.5 mmol ) and K2CO3 ( 1 .6 g; 1 1 .4 mmol) in ACN (18 mL ). The reaction was heated at 80C for 2h. The reaction mixture was partitioned between a saturated solution of NaHCO; and EtOAc. The organic layer was separated, dried over MgS04, filtered and evaporated till dryness. The residue was purified by chromatography ov er silica gel ( Stationary phase: irregular SiOH 40 iim 120g, mobile phase gradient from: 100% DCM, 0% MeOH to 95% DCM, 5% MeOH). The fractions containing product were collected and ev aporated to dryness yielding 1 .6 g (65%) of intermediate 12 .

The chemical industry reduces the impact on the environment during synthesis 1H-Pyrazole-4-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron Nathaniel; (161 pag.)WO2018/50684; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27258-32-8, name is 1-Methyl-1H-pyrazole-3-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 27258-32-8, Recommanded Product: 1-Methyl-1H-pyrazole-3-carbaldehyde

in room temperature, Mix 1-methyl-1H-pyrazole-3-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (4.5 g, 0.03 mol) and 100 g of acetic acid (1.67 mol), add 25 g of ammonia-containing molecular mass concentration 25percent ammonia water and 400 ml water, heated to 90 ° C, the reaction exotherm, maintain the reaction temperature 100 ° C, reflux reaction for 1 hour until 1-methyl-1H-pyrazole-3-carbaldehyde reaction is complete, the reaction solution is cooled to room temperature Pour into ice water to quench and dilute, neutralize until the reaction solution is neutral, extract with ethyl acetate, dry, concentrate the product, distill it under reduced pressure and recrystallize to obtain 8.6 g of product, yield 80percent, purity 98percent the above.

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-pyrazole-3-carbaldehyde, other downstream synthetic routes, hurry up and to see.

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