Tag: M.W=0-100

Synthetic Route of 81945-73-5, 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. 81945-73-5, name is 1H-Pyrazol-1-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 27: Synthesis of 5-Bromo-l-(2,6-difluorobenzyl)-lH-pyrazoIeStep 1: 2-(2,6-Difluorobenzyl)-l-hydroxy-lH-pyrazole1-Hydroxypyrazole (49.3 mg, 0.59 mmol, 1.0 eq) was mixed with 165.8 mg (0.80 mmol, 1.36 eq) of 2,6-difluorobenzyl bromide in -1-2 mL of anhydrous CHCl3 under argon. The mixture was heated at 80 0C for 18 h under inert atmosphere in a sealed flask without condenser. The residue was partitioned between 37 weight percent aqueous HCl and toluene. The aqueous layer was collected and the toluene fraction extracted again with 37 weight percent aqueous HCl. The combined aqueous HCL fractions were neutralized with 5N aqueous NaOH to pH~l 1-12 and then back-extracted with 3 x 30 mL of CHCl3. The organic layers were combined, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield 86.3 mg (70.1% yield) of 2-(2,6- difluorobenzyl)-l -hydroxy- lH-pyrazole as a tan brown solid. 1H NMR (CDCl3 300 MHz) delta 7.37 (m, IH), 7.18 (d, IH), 6.95 (t, 2H), 6.85 (d, IH), 6.11 (t, IH), 5.43 (s, 2.00 H). LC/MS (ES) M+l=211.2Step 2: 5-Bromo-l-(2,6-difluorobenzyl)-lH-pyrazole2-(2,6-Difluorobenzyl)-l -hydroxy- lH-pyrazole (81.2 mg, 0.386 mmol, l.Oeq) and 5ml of anhydrous CHCl3 were combined in a flame-dried 25 mL round-bottom flask under argon and cooled in an ice/water bath. A solution Of POBr3 (398.1 mg, 1.39 mmol, 3.60 eq) in 3 mL of CHCl3 was added using a syringe in aliquots over an hour period with stirring. The reaction solution was warmed to room temperature and stirred for 16 hours. The CHCl3 was removed in vacuo and the resulting orange mixture was neutralized with saturated aqueous NaHCO3 and extracted with 3 x 30 mL of diethyl ether. The combined ether fractions were washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 101.5 mg (96.7% yield) of 5 -bromo-1 -(2,6- difluorobenzyl)- lH-pyrazole as a hygroscopic orange-tan colored solid. 1H NMR (CDCl3 300 MHz) delta 7.51 (d, IH), 7.34 (m, IH), 6.94 (t, 2H), 6.29 (d, IH), 5.50 (s, 2H). LC/MS (ES) M+l= 273.1, 275.1

The synthetic route of 1H-Pyrazol-1-ol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2006/44528; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, 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 31108-57-3 as follows.

Synthesis of II-B14 To a solution of II-B13 (220 mg, 0.53 mmol) in acetone (3 mL) was added 4-cyano-pyrazole (197 mg, 2.1 mmol) and K2C03 (292 mg, 2.1 mmol). After stirring at 25C for 16 h, the reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2 x 10 mL). The combined organic solution was concentrated and purified by prep-HPLC (Instrument: BF; Column: Xtimate C18 l50*25mm*5pm; Condition: water (0.225% FA)-ACN; Begin B: 50; End B: 70; Gradient Time (min): 7.5; 100%B Hold Time (min): 2; FlowRate (mL/min): 30), lyophilized and re-crystallized from MeCN/H20 (20 mL, 1 : 1) to give II-B14 (84 mg, 37%) as a solid. 1H NMR (400 MHz, CDCl3) dH, 7.84-7.78 (m, 2H), 5.07 (d, 7= 18.0 Hz, 1H), 4.95 (d, 7 = 18.6 Hz, 1H), 3.88-3.77 (m, 2H), 3.71 (dd, 7=3.6, 11.6 Hz, 1H), 3.27 (t, 7= 11.6 Hz, 1H), 2.72 (dd, 7=3.6, 11.2 Hz, 1H), 1.89-1.69 (m, 5H), 1.55-1.24 (m, 15H), 1.16-0.99 (m, 6H); LC-ELSD/MS purity 99%, MS ESI calcd. for C25H34N302 [M+H-H20]+ 408.3, found 408.2.

According to the analysis of related databases, 31108-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (206 pag.)WO2019/140272; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1453-58-3,Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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 3-methyl- 1H-pyrazole (500 mg) in acetonitrile (10 mL) were added di-tert-butyl dicarbonate (1.59 g, 1.7 mL) and DMAP (74.4 mg) at 0°C. The mixture was allowed to warm to rt and was stirred for 2 h. Then, EtOAc was added and the mixture was washed with 0.1 N HC1,saturated NaHCO3 solution and brine, dried with Na2504 and evaporated. The crude product(containing -15percent of tert-butyl 5-methylpyrazole-1-carboxylate) was used in the next reaction step without further purification.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HERT, Jerome; HUNZIKER, Daniel; KUEHNE, Holger; LUEBBERS, Thomas; MARTIN, Rainer E.; MATTEI, Patrizio; NEIDHART, Werner; RICHTER, Hans; RUDOLPH, Markus; PINARD, Emmanuel; (450 pag.)WO2017/37146; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 67-51-6, These common heterocyclic compound, 67-51-6, name is 3,5-Dimethyl-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.

In a 250 ml reaction vessel, 3,5-dimethyl-1 H-pyrazole x51 (0.5 g, 5 mmol), I2 (0.79 g, 30 mmol) and CAN (1.71 g, 3 mmol) are dissolved in 70 ml of CH3CN and stirred at room temperature for 16 h. The solvent is evaporated, the residue dissolved in AcOEt and washed with a 10 % aqueous solution of Na2S2U3 and brine. The aqueous phase is re- extracted with AcOEt and the combined organic phases are dried over Na2SO4, filtered and concentrated to dryness to afford 1.15 g (100 %) of crude 4-iodo-3,5-dimethyl-1 H- pyrazole x52, which is used in the next step without further purification.LC-MS (MH+): 223.

Statistics shows that 3,5-Dimethyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 67-51-6.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-13-1, 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 288-13-1 as follows.

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

According to the analysis of related databases, 288-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 31108-57-3, 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 4: 3,5-dibromo-lH-pyrazole-4-carbonitrile To lH-pyrazole-4-carbonitrile (6.76 g, 52.2 mmol) purchased from Aldrich (catalog number CDS008901) were added ethanol (150 mL) and water (225 mL). Then sodium acetate (29.1 g, 355 mmol) was added and the mixture was stirred until solids completely dissolved. Then bromine (10.75 mL, 209 mmol) was added dropwise. After 2 hours the reaction was complete. The reaction was diluted with water then extracted with DCM (3X150ml). The combined organic phases were washed with a saturated aqueous solution of sodilum thiosulfate (Na2S203). Poor layer seperation was observed in separating funnel, so water was added until DCM layer was in the bottom. The organic phase was then dired over MgS04, filtered and concentrated to form a solid. Purification: the solid was first dissolved in EtOAc. When the entire solid was dissolved, additional EtOAc was added to almost double the starting volume. Then hexane was added until solution turned slightly cloudy. After 30 min decantation, the small amount of precipitate formed in the flask was filtered, a dark brown oil left on the filter. The much lighter amber color solution that filtered though was then concentrated and contained mostly the desired product of 3,5-dibromo-lH-pyrazole-4-carbonitrile (8.9 g, 35.5 mmol, 68.0 % yield), it was used without further purification. No proton in the structure (only NH), no NMR spectrum. LCMS: the compound does not ionize.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; NEW YORK UNIVERSITY SCHOOL OF MEDICINE; ALONSO PADILLA, Julio; CHARNLEY, Adam Kenneth; COTILLO TORREJON, Ignacio; ELBAN, Mark; HUGHES, Terry Vincent; KESSLER, Albane Marie; KNAPP-REED, Beth Anne; LIAN, Yiqian; MARTIN, Jose Julio; PENA URQUIZA, Imanol; RODRIGUEZ FERNANDEZ, Ana; (37 pag.)WO2016/55607; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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: C3H3FN2

To a mixture of 60% sodium hydride (56 mg) and THF (15 mL) was added 4-fluoro-1H-pyrazole (103 mg) at 0C. The mixture was stirred at 0C for 1 hr, and to the mixture was added 2,4-difluoro-1l-nitrobenzene (0.110 mL). The mixture was stirred overnight at room temperature, to the mixture was added saturated aqueous ammonium chloride solution at 0C, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (155 mg). MS: [M+H]+226.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 35277-02-2, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; ITO, Masahiro; SUGIYAMA, Hideyuki; KUBO, Osamu; KIKUCHI, Fumiaki; YASUI, Takeshi; KAKEGAWA, Keiko; IKEDA, Zenichi; MIYAZAKI, Tohru; ARIKAWA, Yasuyoshi; OKAWA, Tomohiro; YONEMORI, Jinichi; TOITA, Akinori; KOJIMA, Takuto; ASANO, Yasutomi; SATO, Ayumu; MAEZAKI, Hironobu; SASAKI, Shinobu; KOKUBO, Hironori; HOMMA, Misaki; SASAKI, Minoru; IMAEDA, Yasuhiro; (500 pag.)WO2019/27054; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3, 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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of II-C4 (110 mg, 0.3 mmol) and lH-pyrazole-4-carbonitrile (48.1 mg, 0.5 mmol) in acetone (5 mL) was added K2C03 (71.3 mg, 0.52 mmol). The reaction mixture was stirred at 20C for 16 hrs. The reaction mixture was quenched with saturated NH4Cl (30 mL) and extracted with EtOAc (3 x 20 mL). The combined organic phase was washed with saturated brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to give the product (100 mg) as an oil. The product was purified by flash column (0-30% of EtOAc in PE) to give II-C5 (52.8 mg, 59%) as a solid. (2650) 1H NMR (400 MHz, CDCI3) dH 7.85 (s, 1H), 7.81 (s, 1H), 4.95 (dd, J= 18.0, 48.8 Hz, 2H), 2.59 (t, J= 8.4 Hz, 1H), 2.26-2.15 (m, 1H), 2.08-2.02 (m, 1H), 1.91-1.84 (m, 1H), 1.82-1.58 (m, 7H), 1.53-1.34 (m, 4H), 1.33-1.07 (m, 12H), 1.00-0.88 (m, 1H), 0.87-0.77 (m, 1H), 0.76 (s, 3H), 0.65 (s, 3H); ELSD, purity 99%; MS ESI calcd. for C^HssONs [M+H-H20]+ 420, found 420.

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

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

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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1H-Pyrazole-4-carbonitrile

To a solution of 2-chloro-N-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (15.0 g, 38.8 mmol) in acetonitrile (450 mL) were added 1H-pyrazole-4-carbonitrile (5.41 g, 93.1 mmol) and powdered potassium carbonate (16.1 g, 116 mmol) and it was stirred overnight at 10000. The reaction mixture was concentrated in vacuo and the residue was extractedwith ethyl acetate and water. Pure title compound precipitated and was filtered off (9.09 g20.5 mmol, 53 % yield, 97 % purity), The organic phase was washed with brine and dried over sodium sulfate. Concentration in vacuo led to further crude title compound (9.11 g., app. 60 % purity).LC-MS (Method B): Rt = 1.17 mm; MS (ESIneg): m/z = 442 [M-H]1HNMR (400MHz, DMSO-d6) oe [ppm]: 3.53 (s, 3H), 3.64 (s, 3H), 4.08 (s, 2H), 6.20 (d,1H), 6.29 (dd, 1H), 7.07 (d, 1H), 7.89 (d, 1H), 8.12 (br s, 1H), 8.30 (br s, 1H), 8.41 -8.54 (m, 2H), 9.17 (brs, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 35344-95-7, 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 35344-95-7 as follows.

A solution of 1H-pyrazole-4-carbaldehyde (2.05 g, 21.4 mmoL) and hydroxylamine hydrochloride (1.63 g, 23.5 mmol) in MeOH (50 mL) was stirred at room temperature for 19 hrs. The reaction mixture was concentrated to give 1H-pyrazole-4-carbaldehyde oxime (3.3 g, crude) as a yellow solid.

According to the analysis of related databases, 35344-95-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics