Day: July 23, 2021

Some common heterocyclic compound, 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H5ClF2N2O, 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. Application In Synthesis of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

5-Chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid (Example lib) (I la) (Mb)In a 500 mL round-bottom flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-l-methyl-lH- pyrazole-4-carbaldehyde were taken up in 30 mL of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 mL of water was added to the reaction mixture, followed by 103 mL of a 30% strength solution of hydrogen peroxide in water. During the addition, the temperature was kept below 37 C. The reaction mixture was then stirred at 50 C for 7 h. After cooling, the organic phase was extracted with 100 mL of water. The aqueous phase was acidified to pH 2 using dilute hydrochloric acid. The white precipitate formed was filtered off, washed twice with 20 mL of water and dried. This gave 3.2 g of 5-chloro-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carboxylic acid as a white solid.’H NMR (400 MHz, DMSO- 6) delta ppm : 3.78 (s, 3H); 7.12 (t, 1H, JHF= 53.60 Hz); 13.19 (s, IR (KBr): 1688 cm_1 (C=0); 2200-3200 cm”1 broad;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 660845-30-7, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; BENTING, Juergen; COQUERON, Pierre-Yves; CRISTAU, Pierre; DAHMEN, Peter; DESBORDES, Philippe; DUBOST, Christophe; GARY, Stephanie; GREUL, Joerg; HADANO, Hiroyuki; VORS, Jean-Pierre; WACHENDORFF-NEUMANN, Ulrike; WO2012/65947; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 154471-65-5, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole, 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 154471-65-5, Application In Synthesis of 1-Methyl-3-(trifluoromethyl)-1H-pyrazole

Into a 10-mL sealed tube purged and maintained with an inert atmosphere of argon, was placed a solution of 1-methyl-3-(trifluoromethyl)-1H-pyrazole (10.0 g, 66.62 mmol) and NBS (16.2 g, 66.62 mmol) in DMF (100 mL). The resulting solution was stirred overnight at 50 C. in an oil bath. The reaction was then quenched by the addition of ice water (1 L). The resulting solution was extracted with ether (3×200 mL), the organic layers combined and dried over anhydrous Na2SO4, filtered and then concentrated to provide the desired product as a yellow oil (12.0 g, crude), which was used as is without further purification. 1H NMR (400 MHz, CDCl3): delta 7.46 (s, 1H), 3.94 (s, 3H) ppm.

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

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1384973-12-9,Some common heterocyclic compound, 1384973-12-9, name is 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, molecular formula is C4H3BrN4, 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.

5-amino-3-bromo-1H-pyrazole-4-carbonitrile (3.74 g, 0.02 mol) was added to the reaction flask.Potassium carbonate (5.53 g, 0.04 mol) and DMF (35 mL),Heat to 60 C and stir for half an hour.Add bromoisopropane (2.95 g, 0.024 mmol),Stir at this temperature for 6 hours.Cool, filter, and concentrate to dryness.Extracted with dichloromethane (200 mL),Washed twice with saturated saline solution,Dry over anhydrous sodium sulfate and concentrate the organic phase.The silica gel sample is quickly passed through the column.Obtained white solid 5-amino-3-bromo-1-isopropyl-1H-pyrazole-4-carbonitrile (3a) 2.56 g,Yield: 55.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-3-bromo-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Patent; Huang Chuanman; (18 pag.)CN108530436; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3994-50-1, name is 1-Methyl-4-nitro-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. Safety of 1-Methyl-4-nitro-1H-pyrazole

Example 1 5-chloro-1-methyl-4-nitro-1H-pyrazole To a 500 mL round bottom flask containing 4-nitro-1-H-pyrazole (5 g, 44.2 mmol) was added sodium hydroxide (1M, 200 mL) and dimethyl sulfate (31 mL, 330 mmol). The mixture was stirred at room temperature for 72 h and the mixture was extracted with CH2Cl2 (2*150 mL). The organic layer was separated and the solvent was distilled off to yield 1-methyl-4-nitro-1H-pyrazole as a white solid (4.30 g, 76%). Following WO 2007/99326, to a 500 mL 3-neck-round bottom flask was added 1-methyl-4-nitro-1H-pyrazole (4.30 g, 33.8 mmol) and THF (12 mL). The mixture was cooled to -78 C. and lithium hexamethyldisilazide in THF (1M, 88.4 mL, 90 mmol) was added dropwise via an addition funnel over 20 min. The brown mixture was stirred for 30 min and warmed to -45 C over 30 min. The mixture was cooled back down to -78 C. and hexachloroethane (10.5 g, 44.2 mmol) dissolved in THF (20 mL) was added via an addition funnel over 15 min. The mixture was stirred for 2.5 h, warmed from -78 C to -40 C and the reaction was monitored by LCMS. Upon completion of the reaction, the reaction was quenched with a solution of saturated NH4Cl (150 mL), and ethyl acetate (100 mL) was added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layer was washed with water (150 mL), dried over Na2SO4 and the organic solvent was distilled off. The crude product was purified via flash chromatography (CH2Cl2/7% MeOH) to yield 5-chloro-1-methyl-4-nitro-1H-pyrazole as a white solid (1.40 g, 20%). 1H NMR (400 MHz, CDCl3) delta 8.13 (s, 1H), 3.92 (s, 3H); ESIMS m/z=162.0 (M+1)

The synthetic route of 1-Methyl-4-nitro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Xiaojing; US2011/251176; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 3469-69-0, name is 4-Iodopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

4-Iodo-lH-pyrazole (20.0 g, 103 mmol) is dissolved in anhydrous THF (150 ml) and trimethylsilyl acetylene (72.8 ml, 515 mmol) is added under an inert atmosphere. Diethyl- amine (150 ml), bis-(triphenylphosphine) palladium (II) chloride (10.8 g, 15 mmol) and copper iodide (2.9 g, 15 mmol) are added and the reaction mixture is left to stir at room temperature for 3 hours. The solvent is removed under reduced pressure. The residue is dissolved in diethyl ether and the insoluble impurities are filtered off. The solvent is removed under reduced pressure. The residue is dissolved in methanol and the insoluble impurities removed. The solvent is removed under reduced pressure. The residue is purified by dry flash chromatography on silica gel eluting with a gradient system of diethyl ether : /so-hexane (20:80 to 100:0) to afford the title compound [MH+] 165.07 1H NMR (DMSO) : 0.00(s, 9H), 7.45 (s, IH), 7.90 (s, IH), 12.90 (br s, IH)

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/74925; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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 1192-21-8, category: pyrazoles-derivatives

Compound VIII-1 (200 mg, 0.48 mmol) and1-methyl-1H-pyrazole-5-amine (IX-2) (71 mg,0.73mmol) dissolved in tetrahydrofuran (5mL), cooled to -25 C, added 1N LiHMDS (0.73ml, 0.73mmol), reacted at -25 C for about 3h, to be detected by TLC (dichloromethane: methanol = 25:1) The raw material VIII-1 is completely reacted, and the solvent is evaporated under reduced pressure.The residue was subjected to column chromatography (dichloromethane:methanol = 150:1) to afford white powder (yield: 25.1%

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

Reference:
Patent; China Pharmaceutical University; Xu Yungen; Ji Dezhong; Zhang Lingzhi; Zhu Qihua; Bai Ying; Wu Yaoyao; (41 pag.)CN109608444; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 36650-74-5, name is 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 36650-74-5, Product Details of 36650-74-5

5 g (53.7 mmol) of 1H-pyrazole-3-carbonitrile were dissolved in 12.5 ml of ethanol and 50 ml of chloroform. With cooling using an ice/acetone bath, gaseous hydrogen chloride was introduced for 50 minutes. The cooling bath was then removed and the mixture was stirred for 3 h. During this time, a solid precipitated out, and this was filtered off and washed with chloroform. Drying under high vacuum gave 7.7 g (81% of theory) of the intermediate ethyl 1H-pyrazole-3-carboximidoate hydrochloride.

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; Bayer Pharma Aktiengesellschaft; STRAUB, Alexander; COLLIN, Marie-Pierre; KOCH, Michael; MEYER, Jutta; SCHLEMMER, Karl-Heinz; NISING, Carl Friedrich; BIBER, Nicole; ANLAUF, Sonja; GROMOV, Alexey; WITTWER, Matthias Beat; (185 pag.)US2016/237059; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 the mixture of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1 H-pyrazoLe-4-carbox- amide (Intermediate P6) (0.317 g, 1.51 mmol) and ethyl phenoxyacetate (0.333 g, 1.81 mmol) in n-butanoL (30 mL) sodium ethanolate (21%, 2.815 mL, 7.54 mmcl) was added and the whole was heated at reflux for 24 hours. The productwas isolated by extraction with ethyl acetate. Organic Layer was dried with sodium sulphate. After concentration, product was purified by chromatography on silicagel (chloroform/methanol, gradient 99:1 to 96:4). 0.137 g of the title product as an amorphous, colorless solid were obtained (yield 28.4%).1H NMR (300MHz, DMSO-d6): delta 12.37 (s, 1H), 8.09 (s, 1H), 7.31 (dd, J = 10.7, 5.4Hz, 2H), 7.13 – 6.90 (m, 3H), 5.03 (s, 2H), 4.88 – 4.68 (m, 1H), 3.95 (dd, J = 11.4, 3.6 Hz, 2H), 3.49 (t, J = 11.2 Hz, 2H), 2.09 (qd, J = 12.3, 4.5 Hz, 2H), 1.80 (dd, J = 12.4, 2.3 Hz, 2H).13C NMR (75 MHz, DMSO-d6): delta 157.72, 157.69, 155.39, 150.96, 134.23, 129.51,121.41, 114.87, 104.88, 67.20, 65.97, 53.18, 31.96.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; CELON PHARMA S.A.; MOSZCZY?SKI-P?TKOWSKI, Rafa?; BOJARSKI, ?ukasz; STEFANIAK, Filip; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/16789; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10250-63-2, name is Ethyl 1-methyl-3-phenyl-1H-pyrazole-5-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 10250-63-2, Application In Synthesis of Ethyl 1-methyl-3-phenyl-1H-pyrazole-5-carboxylate

Production Example 197c) 0.12 g of ethyl 1-methyl-3-phenyl-1H-5-pyrazolecarboxylate was dissolved in 5 ml ethanol. 1 ml of 5N aqueous sodium hydroxide solution was added thereto, followed by heating under reflux for 1 hour. The reaction solution was ice-cooled, neutralized with 2N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to give 0.11 g of 1-methyl-3-phenyl-1H-5-pyrazolecarboxylic acid. 1H-NMR(CDCl3) delta: 4.22(s, 3H) 7.22(s, 1H) 7.33(t, J=8.0Hz, 1H) 7.40(t, J=8.0Hz, 2H) 8.80(d, J=8.0Hz, 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; Eisai Co., Ltd.; EP1216980; (2002); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 31108-57-3, These common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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 of II-F10 (49.4 mg, 0.1 mmol) and lH-pyrazole-4-carbonitrile (22.3 mg, 0.2 mmol) in acetone (2 mL) was added K2C03 (33.1 mg, 0.24 mmol). After stirring at 20 C for 16 h, the reaction mixture was extracted with EtOAc (3 x 30 mL). The combined organic solution was washed with saturated brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash column (0-20% of EtOAc in PE) to give II- Fll (28.5 mg, 56%) as a solid. (2792) 1H NMR (400 MHz, CDCl3) dH 7.85 (s, 1H), 7.81 (s, 1H), 5.06-4.86 (dd, J= 17.6, 47.6 Hz, 2H) , 2.60 (t, j= 8.8 Hz), 2.27-2.15 (m, 1H), 2.06-1.99 (m, 1H), 1.84-1.67 (m, 6H), 1.56- 1.37 (m, 8H), 1.33-0.80 (m, 13H), 0.67 (s, 3H); LC-ELSD/MS purity 99.30%, MS ESI calcd. for C26H36N30[M-H20+H]+ 406.29, found 406.3.

The synthetic route of 31108-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (646 pag.)WO2019/126761; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics