Tag: M.W:100-200

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

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: 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

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

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

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. 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methyl-1-phenyl-1H-pyrazole

General procedure: In a typical experiment,the aryl bromide (3 mmol), heteroaromatic 1, 21 or 23 (1 mmol), KOAc(0.588 g, 6 mmol) and PdCl(C3H5)(dppb)16 (0.012 g, 0.02 mmol) were dissolvedin DMA (4 mL) under an argon atmosphere. The reaction mixture was stirred at 150 C for 72 h. Then, the solvent was evaporated and the product was purified by silica gel column chromatography.

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:
Article; Takfaoui, Abdelilah; Zhao, Liqin; Touzani, Rachid; Dixneuf, Pierre H.; Doucet, Henri; Tetrahedron Letters; vol. 55; 10; (2014); p. 1697 – 1701;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, 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 of2,4-difluoro-l-nitrobenzene (1.76 g, 11.1 mmol) and DIEA (1.93 ml, 11.1 mmol) in THF (20 ml) was added dropwise the solution of 5-cyclopropyl-1H-pyrazol-3- amine (0.91 g, 7.39 mmol) in THF (5 ml) at 25 C. After addition, the reaction mixture was stirred at 80 C for 48 hrs. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane : DCM : EtOAc = 2 : 1 : 1) to give the title compound as a yellow solid (0.62 g, 32%). NMR (400 MHz) 12.37 (s, 1H), 9.83 (s, 1H), 8.25 (m, 1H), 7.98 (d, J= 11.2 Hz, 1H), 6.75 (m, 1H), 5.95 (s, 1H), 1.90 (m, 1H), 0.96 (m, 2H), 0.72 (m, 2H).

Statistics shows that 5-Cyclopropyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 175137-46-9.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/103010; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 154471-65-5, 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 154471-65-5 as follows.

Preparation 7[1 -Methyl-3-(trifluoromethyl)-1 H-pyrazol-5-yllboronic acidTo a stirred solution of 1 -methyl-3-(thfluoronnethyl)-1 H-pyrazole (1 .89 g, 12.6 mmol) in anhydrous tetrahydrofuran (20 ml_) under nitrogen cooled to -78C was added n- butyllithium (8.3 mL, 1 .6 M solution in hexanes, 13.2 mmol) slowly over 5 minutes. The resulting yellow solution was stirred at -78C for 1 hour and trimethyl borate (1 .56 mL, 13.9 mmol) was then added slowly. The reaction flask was covered in foil and allowed to warm to room temperature for 16 hours. The white solution was quenched with aqueous 1 M hydrogen chloride solution (10 mL) and stirred at room temperature for 1 .5 hours. The mixture was extracted with ethyl acetate (2 x 30 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo to give an off-white foam (2.1 1 g). The foam was triturated with dichloromethane, filtered and dried in vacuo to afford the title compound as a white solid (1 .57 g, 64%).1H NMR (400 MHz, MeOH-d4): delta 4.04 (s, 3H), 6.89 (s, 1 H).LCMS Rt = 1 .1 1 minutes MS m/z 194 [MH]+ 192 [M-H]-,

According to the analysis of related databases, 154471-65-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; BROWN, Alan, Daniel; RAWSON, David, James; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2012/7868; (2012); 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. 4522-35-4, name is 3-Iodo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C3H3IN2

To a mixture of 180 (193.97mg, i.OOrnrnol) and 28 (139.10mg, i.OOrnmol) in DMF (5rnL), was added C52CO3 (325.82mg, 1 .OOmmol) in one portion at room temperature. The mixture was then heated to 80uC for 1 5 hours under N2 atmosphere. ILC showed the reaction was completed. Themixture was cooled to room temperature and was then poured into water (i5mL) slowly. A white solid precipitated out from the mixture, filtered off. The solid was dried to afford product 197 (300.00 mg, yield: 67.08%).LCMS: m/, 313.9 (M±H.

According to the analysis of related databases, 4522-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; JIN, Xiaowei; (176 pag.)WO2017/117708; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 71229-85-1, 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. 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 6-chloro-7-fluoro-1H-indole 8 (400 mg, 2.36 mmol) in toluene (10 mL) were added 4-bromo-1-ethyl-1H-pyrazole 4 (Step 3 above; 414 mg, 2.36 mmol), potassium phosphate (1.25 g, 5.91 mmol), N,N’-dimethylethylenediamine (84 mg, 0.95 mmol) and Cu(I)I (45 mg, 0.24 mmol) at RT under inert atmosphere. The resulted solution was purged with argon and sealed the tube. The reaction mixture was then heated to 140 C. for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT, diluted with hexane (10 mL) and filtered through a short pad of celite. The filtrate was washed with water (2*10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified (silica gel chromatography; 8-10% EtOAc/Hexanes) to afford compound 9 (224 mg, 36%) as a light brown thick liquid. 1H NMR (500 MHz, CDCl3): delta 7.64 (s, 1H), 7.61 (s, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.12-7.07 (m, 2H), 6.60-6.59 (m, 1H), 4.22 (q, J=7.5 Hz, 2H), 1.55 (t, J=7.5 Hz, 3H); LC-MS (ESI): 94.7%; m/z 264.1 (M+H+); (column: X Select C-18, 50*3.0 mm, 3.5 mum); RT 3.87 min; 5 mM NH4OAc: ACN; 0.8 mL/min).

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

Reference:
Patent; PHARMAKEA, INC.; Evans, Jillian Frances; US9051320; (2015); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics