Day: July 5, 2021

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-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 2075-46-9, category: pyrazoles-derivatives

General procedure: A mixture of methyliodide (12 mmol), 1a (6 mmol) and K2CO3 (9 mmol) in DMF (6 mL) was stirred overnight at room temperature. Then the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (25 mL × 3). The organic layer was washed with aqueous saturated sodium bicarbonate, dried by sodium sulfate, ltered and concentrated in vacuum. Purication by ash column chromatography gave the desired product 2a (2a-2c).A mixture of iodobenzene (6.82 mmol), 1a (0.70 g, 6.20 mmol), 8-hydroxyquinoline (0.09 g, 0.62 mmol), cuprous iodide (0.18 g, 0.62 mmol) and potassium carbonate (1.73 g, 12.40 mmol) in DMSO (10 mL) was heated at 135 oC for 20 h. After cooling to room temperature, the reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate, dried by sodium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography gave the desired products 2d (2d-2g).

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-Nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Chen-Ru; Wang, Ze-Feng; Shi, Lu; Wang, Zhong-Chang; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2382 – 2390;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, molecular formula is C4H5ClN2O2S, 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. name: 1-Methyl-1H-pyrazole-4-sulfonyl chloride

General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.11 1-Methyl-N-{1-[2-(biphenyl-2-yloxy)ethyl]piperidin-4-yl}-N-methyl-1H-pyrazole-4-sulfonamide (20) Yellow oil, 100 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.7); LC/MS purity 100%, tR = 4.65, C24H30N4O3S, MW 454.58, Monoisotopic Mass 454.20, [M+H]+ 455.5. 1H NMR (300 MHz, CDCl3) delta 1.40-1.48 (m, 2H), 1.62-1.65 (m, 2H), 2.05 (td, J = 11.90, 2.20 Hz, 2H), 2.66-2.70 (m, 2H), 2.71 (s, 3H), 2.83-2.90 (m, 2H), 3.68-3.80 (m, 1H), 3.94 (s, 3H), 4.04 (t, J = 5.63 Hz, 2H), 6.93-6.97 (m, 1H), 7.03 (td, J = 7.45, 1.06 Hz, 1H), 7.28-7.33 (m, 3H), 7.34-7.40 (m, 2H), 7.49-7.51 (m, 1H), 7.51-7.53 (m, 1H), 7.69 (d, J = 0.54 Hz, 1H), 7.73 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 28.59, 29.19, 39.57, 53.35, 55.00, 56.78, 66.94, 112.70, 121.18, 122.22, 126.83, 127.79, 128.58, 129.61, 130.86, 131.13, 131.35, 138.17, 138.48, 155.63. Anal. calcd for C24H30N4O3S·HCl: C: 58.70, H: 6.36, N: 11.41, S: 6.53; Found C: 58.96, H: 6.49, N: 11.42, S: 6.88. Mp for C24H30N4O3S·HCl: 189.5-189.9 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288148-34-5, its application will become more common.

Reference:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
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

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

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

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

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

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

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

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