Category: pyrazoles-derivatives

Electric Literature of 34334-96-8, These common heterocyclic compound, 34334-96-8, name is 3-Methyl-5-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.

Example 7 Preparation of 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol A solution of 5-methyl-3-nitro-1H-pyrazole (500 mg, 3.93 mmol) and potassium carbonate (1.08 g, 7.81 mmol) in acetonitrile (20 mL) was treated dropwise with 2-iodoethanol (2.00 g, 11.6 mmol) and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, heptane to 1:1 ethyl acetate/heptane) to afford 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol as a white solid: 1H NMR (400 MHz, DMSO-d6.) d 6.82 (s, 1H), 4.97 (t, J=5.2 Hz, 1H), 4.19 (t, J=5.2 Hz, 2H), 3.75 (q, J=5.2 Hz, 2H), 2.35 (s, 3H).

The synthetic route of 34334-96-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gilead Connecticut, Inc.; Blomgren, Peter A.; Currie, Kevin S.; Kropf, Jeffrey E.; Lee, Seung H.; Mitchell, Scott A.; Schmitt, Aaron C.; Xu, Jianjun; Zhao, Zhongdong; US2014/148430; (2014); 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

Reference of 1190380-49-4, 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. 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

Compound 11.4 (70 mg, 0.20 mmol, 1.00 eq.) and 1-(oxan-4-yl)-1H-pyrazol-4-amine (52 mg, 0.31 mmol, 1.50 eq.) were dissolved in HCl in dioxane (0.2 mL, 4N) and n- BuOH (2 mL). The reaction was stirred for 6 h at 110 C. The solids were collected by filtration and dissolved in H20. The pH value of the solution was adjusted to 10 with Na2CC”3. Precipitated solids were collected by filtration to provide 45.3 mg (47%) of compound I-17 as an off-white solid. LC-MS (ESI, w/z):[M+H+]+= 483; 1H NMR (300 MHz, DMSO-d6): delta 8.93 (s, 1H), 7.98 (s ,1H) , 7.50 (s, 1H), 6.85 (s, 1H), 4.44 (m, 4H) , 4.12 (m, 1H), 3.96 (m, 2H), 3.56 (t, 4H), 3.48 (m, 2H), 2.50 (m, 4H), 2.25 (m, 1H), 1.91-2.07 (m, H), 1.28-1.60 (m, 4H).

The chemical industry reduces the impact on the environment during synthesis 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NIMBUS IRIS, INC.; ROMERO, Donna; ROBINSON, Shaughnessy; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; BOYCE, Sarah; (135 pag.)WO2017/4133; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 5334-43-0, name is 5-Amino-1-phenyl-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. Safety of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

EXAMPLE 2 1-Phenyl-4-cyano-5-(phenylureido)-pyrazole STR107 9.0 g (80 mmol) of potassium tert-butylate and 8.7 ml (80 mmol) of phenyl isocyanate were added to a solution of 5.52 g (30 mmol) of 1-phenyl-4-cyano-5-aminopyrazole in 100 ml of toluene. The mixture was heated for 15 hours at 80 C. and then cooled, the insoluble constituents were separated off and the resulting solution was acidified with acetic acid, the product crystallizing out. Yield: 96%.

The synthetic route of 5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US5486618; (1996); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

14521-80-3, name is 3-Bromo-1H-pyrazole, 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. category: pyrazoles-derivatives

Methyl N-[(2-methyl-5-iodophenyl)methyl]carbamate (i.e. the product of Example 3, Step C) (5.00 g, 16.4 mmol), 3-bromopyrazole (3.11 g, 21.3 mmol), potassium carbonate (5.65 g, 41.0 mmol), and copper (I) iodide (623 mg, 3.28 mmol) were combined in toluene (16 mL) and N,N’-dimethylformamide (16 mL). A stream of nitrogen gas was bubbled into the mixture for 30 min., N,1ST -dimethyl- 1 ,2-cyclohexanediamine (1.0 mL, 6.6 mmol) was added and a stream of nitrogen gas was bubbled through the mixture for an additional 30 min. The nitrogen line was then raised above the reaction mixture and the mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered through a fritted- glass funnel and then concentrated under vacuum. The resultant residue was purified by medium pressure liquid chromatography using a gradient of 10 to 50% ethyl acetate in hexanes to provide the title compound (4.35 g) as an off- white solid. in NMR (500 MHz, CDC13) delta 7.76 (d, J=2.5 Hz, 1 H), 7.55 (d, J=2.0 Hz, 1 H), 7.42 (dd, J=8.1, 2.0 Hz, 1 H), 7.23 (d, J=8.2 Hz, 1 H), 6.45 (d, J=2.6 Hz, 1 H), 5.00 (bs, 1 H), 4.40 (d, J=5.7 Hz, 2 H), 3.71 (s, 3 H), 2.34 (s, 3 H).

The synthetic route of 14521-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; TAGGI, Andrew, Edmund; DIETRICH, Robert, F.; MARCUS, Kimberly, Katherine; MCCANN, Stephen, Frederick; WO2014/66120; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-46-9, 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 2075-46-9 as follows.

To a solution of 4-nitro-lH-pyrazole (1.13 g, 10.0 mmol) and iodomethane (1.25 mL, 20.0 mmol) in DMF (12 mL), NaH (60% in mineral oil, 0.600 g, 15.0 mmol) was added. The mixture was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with water, dried over Na2S04, concentrated in vacuo to give l-methyl-4- nitro-lH-pyrazole as a solid (1.11 g).

According to the analysis of related databases, 2075-46-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; JIA, Zhaozhong, J.; SONG, Yonghong; XU, Qing; KANE, Brian; BAUER, Shawn, M.; PANDEY, Anjali; WO2012/61418; (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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 31728-75-3

To a 0C solution of 1 ,5-dimethyl-lH-pyrazole-4-carboxylic acid (1.0 g, 7.14 mmol) in DCM/MeOH (7 mL each) was added 2M TMSCHN2 in hexane (4.28 mL, 8.56 mmol). The reaction mixture was stirred at 0C for 1 h, then was allowed to warm to RT and stirred at RT overnight, then was concentrated in vacuo. The crude product was chromatographed (80 g Si02; continuous gradient from 0% to 50% EtOAc in hexane over 20 min) to give the title compound (900 mg, 5.84 mmol, 82 % yield). LCMS, [M + H]+ = 155.2.

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 31728-75-3.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; LI, Jun; SHI, Yan; WANG, Ying; ZHANG, Hao; KENNEDY, Lawrence J.; WALKER, Steven J.; REDDIGUNTA, Ramesh Babu; (138 pag.)WO2019/126098; (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

Reference of 37622-90-5, 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 37622-90-5 as follows.

To a solution of 20 (14.0 g, 100 mmol) and NaOAc (32.8 g,400 mmol) in EtOH/H2O (200 mL, v/v, 2/3) was added Br2 (39.95 g,250 mmol) at room temperature. The mixture was stirred at room temperature for 10 h. After addition of Na2S2O3 (31.62 g, 200 mmol)was added and the resulting mixture was then concentrated to afford the crude product, the mixture was poured into H2O at room temperature and was extracted with EtOAc. The organic layer was separated,washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 21 (26.6 g,92%) as a pale yellow solid. MS (ESI) m/z: 296.7 [M+H]+.

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yin, Yuan; Chen, Cheng-Juan; Yu, Ru-Nan; Shu, Lei; Zhang, Tian-Tai; Zhang, Da-Yong; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1562 – 1576;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1572-10-7, name is 3-Amino-5-phenylpyrazole, 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. Quality Control of 3-Amino-5-phenylpyrazole

To a cold (0C) solution of 3-amino-5-phenylpyrazole (10.0 g, 62.8 mmol) in toluene (100 mL) was added ethoxycarbonyl isothiocyanate (8.3 mL, 70 mmol) dropwise via a pressure equalizing funnel. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15 hours, at which time a heavy white precipitate had formed. The precipitate was collected by filtration and dried to give ethyl [ (3-phenyl-1 H-pyrazol-5-yl) amino] carbothioylcarbamate (11 g, 60%) as a white solid.’H-NMR (DMSO-d6) : 8 13.25 (s, 1H), 12.06 (s, 1 H), 11.40 (s, 1H), 7.75 (d, 2H), 7.5-7. 3 (m, 4H), 4.25 (q, 2H), 1.29 (t, 3H); MS m/z 291 (M+1).

The synthetic route of 3-Amino-5-phenylpyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/76441; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics