Day: May 14, 2021

128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, 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. name: 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Chemical synthesis of compound 16677. For synthesis of compound 16677, 1-methyl-3-trifluoromethyl-5-pyrazolecarboxylic acid 3 (Scheme 1, FIG. 10) was prepared from commercially available compound 1 as previously described (Schlosser et al., (2002) Eur. J. Org. Chem. 2002(17), 2913-2920). Compound 3 (820 mg, 4.2 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (2.0 M in CH2Cl2, 8.5 mmol, 4.2 ml) and a catalytic amount of DMF. The reaction mixture was incubated at room temperature for 5 hours. Evaporation of solvent delivered yellow acyl chloride 4 in quantitative yield.

The synthetic route of 128694-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Plemper, Richard K.; Snyder, James P.; Sun, Aiming; US2011/160188; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 796729-10-7, The chemical industry reduces the impact on the environment during synthesis 796729-10-7, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

Add 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (0.81 g, 5.3 mmol) and 15 mL of 1,4-dioxane, benzyl alcohol to a 50 mL single-mouth vial (0.83 mL, 8.0 mmol), DIPEA (1.8 mL, 11.0 mmol), and DPPA (2.20 g,8.0 mmol), refluxing at 110 C overnight, the reaction was completed by TLC, cooled to 0 C, suction filtration,Obtained 0.98 g of a pale yellow solid in a yield of 72%.

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, 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Lin Xinglong; Xie Hongming; Hu Yangxiao; Li Shiguang; Zhang Yingjun; Tan Yumei; Yuan Mingyun; (124 pag.)CN108948019; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 128694-63-3,Some common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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 1: l-Methyl-3-(trifluoromethyl)-lH-pyrazol-5-yl] methanol Borane (1M in THF; 9.0 mL, 9.0 mmol) was added to a solution of l-methyl-5- (trifluoromethyl)pyrazole-3-carboxylic acid (350 mg, 1.8 mmol) in THF (10 mL) at rt. The mixture was stirred was stirred for 3 hours. It was then cooled to 0 C and quenched with water. The mixture was extracted with EtOAc (3x) and the combined organic layers were washed with brine, dried over Na2SC>4, filtered, and concentrated. The residue was purified on silica gel to afford [l-methyl-3-(trifluoromethyl)- lH-pyrazol-5-yi]methanol (188 mg; 58%) as a colorless oil. LCMS (FA): m/z = 18l (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 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 40711-33-9, name is Ethyl 5-oxo-2,5-dihydro-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 40711-33-9, Application In Synthesis of Ethyl 5-oxo-2,5-dihydro-1H-pyrazole-3-carboxylate

To a suspension of ethyl 5-oxo-2,5-dihydro-1 H-pyrazole-3-carboxylate (1.5 g, prepared with an analogous procedure to that described in Preparation 1 ) and Na2CO3 (1.22 g) in dry DMF (20 ml_), [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (1.11 ml.) was added drop wise and the mixture was stirred at 60 0C overnight. The reaction mixture was cooled down to rt and filtered to remove the Na2CO3. The filtrate was diluted with DMF and Na2CO3 (1.22g) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (2.1 ml.) were added and the mixture was stirred at 60 0C for additional 36h. After cooling, the mixture was diluted with Et2O, washed with chilly water, dried, filtered and evaporated under reduced pressure. The crude was dissolved in DCM (15 ml.) and 2,6-lutidine (1.08 ml.) and [(3-bromoethyl)oxy](1 ,1-dimethylethyl)dimethylsilane (0.86 ml.) were added at 0 0C and the mixture was stirred at rt for 1 h. The mixture was diluted in DCM, washed with NaHCO3sat and then with HCI 0.25N. The organic layer was dried and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography on silica column eluting with Cy/AcOEt with a gradient of Cy from 100% to 80% to give the title compound as colourless oil (0.63 g).MS (m/z): 315 [MH]+.

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; GLAXO GROUP LIMITED; WO2009/130232; (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. 304693-70-7, name is 1-(2-Methoxyethyl)-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 304693-70-7

To a solution of Intermediate 47 (300 mg, 0.44 mmol) in dichloromethane (5 mL) was added intermediate 50 (80.0 mg, 0.530 mmol) and NaBH(OAc)3 (186 mg, (0941) 0.880 mmol). After stirring at room temperature overnight, the mixture was concentrated to give a residue which was purified by prep-HPLC (Waters 2767/Qda, Column: Waters Xbridge 19* 150mm lOum, Mobile Phase A: H20 (0.1%NH4OH), B: ACN) to yield Compound 97 (53.0 mg, 24.6% yield) as yellow oil. (0942) NMR CDCI3 (400 MHz): delta 8.42 (s, 1H), 7.42 (s, 1H), 7.38 (s, 2H), 4.26 (t, J= 5.2 Hz, 2H), 3.91-3.83 (m, 3H), 3.75-3.73 (m, 3H), 3.64 (q, J= 10.4 Hz, 2H), 3.43 (s, 2H), 3.33 (s, 3H), 2.54-2.49 (m, 4H), 2.37-2.32 (m, 2H), 1.86-1.80 (m, 1H), 1.70-1.63 (s, 1H).

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 304693-70-7.

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

Related Products of 1031351-95-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1031351-95-7 name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 2: To a solution of the chloro-phosphonium salt (2.9 g, 5.95 mmol) in dry THF (20 mL) at – 78 0C was added LiHMDS (6.54 mL, 6.54 mmol) and the resulting mixture stirred at -78 0C for 1 h. The mixture was then warmed up to room temperature and a solution of lH-pyrazole-5- carboxylic acid, 3-formyl-l -methyl-methyl ester (1.0 g, 5.95 mmol) in dry THF (15 mL) was added and the resulting mixture stirred for 2 h. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (2 x 40 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate 1 :0 to 9:1) afforded, two products, 5-{(Z)-2-[3-(4- fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl} -2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (400 mg) and ethyl 5-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester (2.15 g) as off white solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); 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 1904-24-1 as follows. Safety of 3-Amino-5-ethylpyrazole

A. 4-(2,4-dichlorophenyl)-7-ethyl-2-methyl-pyrazolo[1,5-a]-1,3,5-triazine A mixture of 3-amino-5-ethylpyrazole (10.3 g, 39.3 mmol) and N-(1-(methylthio)ethylidene)-2,4-dichloro-benzamide (4.0 g, 35.7 mmol) in anhydrous dioxan (20 mL) was stirred at reflux temperatrue under a nitrogen atmosphere for 16 h. After being cooled to ambient temperature, the reaction mix was concentrated in vacuo and the residue was treated with dichloromethane. The resulting supsension was filtered and the filtrate was concentrated in vacuo to afford an oil (1.5 g, 14% yield): NMR (CDCl3, 300 MHz): delta 7.62 (d, 1H, J=8), 7.59 (d, 1H, J=2), 7.45 (dd, 1H, J=8,2), 6.42 (s, 1H), 2.82 (q, 2H, J=8), 2.73 (s, 3H), 1.30 (t, 3H, J=8).

According to the analysis of related databases, 1904-24-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilligan, Paul J.; Wilde, Richard G.; US2002/147338; (2002); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1125828-30-9, name is 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone, 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. Formula: C12H8ClF3N2O

A 3L 3-neck jacketed round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged sequentially with dichloro(pentamethylcyclopentadienyl)iridium (III) dimer ([Cp*IrCl2]2, STREM, CASNo.: 12354-85-7, 34 mg, 0.043 mmol), (1R,2R)-(-)-N-(4-toluenesulfonyl)-1,2-diphenylethylenediamine (STREM, CASNo.: 144222-34-4, 32 mg, 0.087 mmol), and water (400 mL, 4×) at room temperature. The resulting mixture was stirred for 3 hours at 40 C. to give a homogeneous orange solution. To this active catalyst solution was added potassium formate (145.5 g, 1.73 mol) and a solution of the ketone 1-(4-chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone (100 g, >99% purity by GC, 0.346 mol) in CH3CN (500 mL, 5×) at 40 C. The reaction mixture was then stirred at 40 C. for 2 hours at which time the reaction was determined to be complete by GC. After cooling to 30 C., the aqueous layer (ca. 480 mL) was removed. The organic layer (ca. 600 mL, 6×) was treated with activated carbon (Darco G-60, 20 g, 0.2×) at 45 C. for 2 hours and filtered through ¼ inch bed of Celpure P65 (USP-NF, Pharmaceutical grade, Sigma) and washed with CH3CN (200 mL, 2×). The filtrate was concentrated to 250 mL (2.5×) and transferred to a 2 L 3-neck jacketed round bottom flask equipped with a mechanical stirrer and a temperature controller. More CH3CN (50 mL, 0.5×) was added to increase the solution volume to 300 mL (3×). This solution was warmed to 60 C. and water (500 mL, 5×) was added to this solution at the same temperature. After stirring for 15 minutes at 60 C., the resulting emulsion-like milky mixture was slowly cooled to room temperature. The crystals were then filtered at room temperature, and washed with CH3CN/water (1:2, 150 mL, 1.5×). The wet cake (108 g, KF: 8.83%) was dried under vacuum at 45 C. for 4 hours to afford the desired alcohol (white solid, 95 g, 94% yield, >99% chemical purity, >99% ee, KF: 0.014%). M.p.: 120 C. (DSC onset temperature); 1H NMR (methanol-d4, 400 MHz) delta 2.19 (br. s., 3H), 5.23 (dd, 6.8 Hz, 7.2 Hz, 1H), 6.19 (d, 2.4 Hz, 1H), 7.29 (d, 2 Hz, 1H), 7.42 (dd, 2.0 Hz, 6.4 Hz, 1H), 7.59 (d, 2.4 Hz, 1H), 7.68 (d, 8.4 Hz, 1H). 13C NMR (methanol-d4) delta 13.4, 67.2, 108.3, 121.7, 124.5, 127.4, 130.1, 131.9, 134.1, 136.4, 141.6, 152.3. LC/MS: MH+=291.

The synthetic route of 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bednarz, Mark S.; Burgoon, JR., Hugh Alfred; Iimura, Shinya; Kanamarlapudi, Ramanaiah C.; Song, Qiuling; Wu, Wenxue; Yan, Jie; Zhang, Haiming; US2009/62540; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 150712-24-6, name is 5-Benzyl-1H-pyrazol-3-amine, molecular formula is C10H11N3, 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. Product Details of 150712-24-6

The solution of 2, 4,5-trichloropyrimidine (0.150 g, 0.82 mmol), 5-benzyl-2H-pyrazol- 3-ylamine (Method 27; 0.129 g, 0.74 mmol), and triethylamine (0.155 ml, 1.12 mmol) in EtOH (5 ml) was heated to55 C for 5 hours and then stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. The resulted yellow solid was stirred in hexanes: ether solution (1: 1), collected by filtration, and then recrystallized from DCM to give the title compound (0.212 g,89%).’H NMR (400 MHz, CDC13)6 4.10 (d, J= 15.2 Hz, 2 H), 6.89 (s, 1 H), 7.27-7. 37(m, 5 H), 8. 28 (s, 1 H). MS: Calcd.: 319; Found:[M+H] + 320

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150712-24-6, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/49033; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 75092-30-7,Some common heterocyclic compound, 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H5IN2O2, 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 65(4-lodo-2-meth -2H-pyrazol-3-yl)methanolTo a solution of 4-iodo-2-methyl-2H-pyrazole-3-carboxylic acid (1.0 g, 3.96 mmol) in tetrahydrofuran (10 mL), under an atmosphere of nitrogen, was added carbonyl diimidazole (0.78 g, 4.36 mmol, 1.1 eq.). The resulting mixture was stirred at room temperature for 1.5 hr before adding sodium borohydride (0.75 g, 19.8 mmol, 3.0 eq.) followed by a solution of methanol in tetrahydrofuran (5 mL), dropwise over a period of 10 min. The resulting mixture was stirred for 3hr before quenching with 2M aqueous hydrochloric acid (30 mL). This mixture was partition with ethyl acetate (50 mL). The organic phase was washed with 1 aqueous sodium hydrogen carbonate (20 mL), saturated brine (20 mL) and dried over sodium sulphate. The resulting mixture was filtered and the filtrate concentrated under reduced pressure to give the title compound as a brown oil (0.56 g, 60%). 1H N R (400 MHz, DMSO-d6) delta ppm 3.87 (s, 3 H) 4.48 (d, J=5.47 Hz, 2 H) 5.30 (t, 1 H) 7.42 (s, 1 H)

The synthetic route of 75092-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics