Category: 31108-57-3

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.

Synthesis of II-A13b To a solution of II-A12b (200 mg, 0.5 mmol) in acetone (3 mL) was added 4-cyanopyrazole (69.9 mg, 0.8 mmol) and K2C03 (345 mg, 2.5 mmol). The mixture was stirred at 25C for 16 hrs. To the mixture was added water (20 mL) and the mixture was extracted with EtOAc (2 x 20 mL). The organic layer was separated, concentrated and purified by flash column (0781) (25-60% EtOAc in PE) to give II-A13b (100 mg). The material (100 mg) was purified by HPLC separation to give II-A13b (4 mg, 2%) as a solid. (0782) 1H NMR (400 MHz, CDCf) dH 7.85-7.80 (m, 2H), 5.38-5.09 (m, 2H), 4.05 (t, J =1.6 Hz, 1H), 3.98 (s, 1H), 3.67 (dd, J= 8.0, 12.0 Hz, 1H), 1.95-1.66 (m, 7H), 1.52-1.37 (m, 8H), 1.35-1.19 (m, 7H), 1.17-1.00 (m, 1H), 0.86 (s, 3H); LC-ELSD/MS purity 99%, MS ESI calcd. for C^^NsOs [M +H]+ 412.2, found 412.2.

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.; (206 pag.)WO2019/140272; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31108-57-3, The chemical industry reduces the impact on the environment during synthesis 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of IV-B8 (44 mg, 0.11 mmol) in acetone (2 mL) was added lH-pyrazole-4- carbonitrile (16 mg, 0.17 mmol) and K2C03 (48 mg, 0.34 mmol). After stirring at 25C for 12 h, the mixture was diluted with water (5 mL) and extracted with EtOAc (2 x 10 mL). The combined organic solution was washed with brine (5 mL), dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by flash column (0-43% of EtOAc in PE) to give IV-B9 (22 mg, 49%) as a solid. (3084) 1HNMR (400 MHz, CDCl3) dH 7.86 (s, 1H), 7.81 (s, 1H), 5.08-5.02 (m, 1H), 4.94-4.87 (m, 1H), 2.63 (t, j= 8.8 Hz, 1H), 2.26-2.16 (m, 1H), 2.06-1.99 (m, 1H), 1.82-1.70 (m, 6H), 1.46- 1.17 (m, 15H), 0.91-0.83 (m, 2H), 0.65 (s, 3H). LC-ELSD/MS purity 99%, MS ESI calcd. for C24H33N302 [M+H]+396.2, found 396.2

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, 1H-Pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H3N3

To a solution of A26 (300mg, 729 umol, 1.00 Eq) in acetone (5 mL) was added K2CO3 (200 mg, 1.45 mmol, 2.0 Eq) and 1H-pyrazole -4-carbonitrile (81.3 mg, 874 umol, 1.2 Eq) at 25oC. The reaction mixture was stirred at 25C for 16 hrs. Then, TLC showed the material was disappeared. The mixture was diluted with water (20 mL) and extracted with EA (30 mL×2). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuum. The residue was purified by silica gel chromatography( 100-200 mesh silica gel, petroleum ether/ethyl acetate =2/1) to afford A39 (245 mg, 549 umol) as a off-white solid. 1H NMR (A39): 400MHz delta 7.86 (s, 1H), 7.81 (s, 1H), 5.04-4.88 (m, 2H), 2.62-2.58 (m, 1H), 0.95 (s, 3H), 0.65 (s, 3H).

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.; MARTINEZ BOTELLA, Gabriel; SALITURO, Francesco, G.; ROBICHAUD, Albert, Jean; HARRISON, Boyd, L.; (275 pag.)WO2016/61527; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31108-57-3, name is 1H-Pyrazole-4-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 31108-57-3, Quality Control of 1H-Pyrazole-4-carbonitrile

General procedure: The appropriate carboxylic acid (1.0 equiv) was treated with oxalylchloride (1.1 equiv) in CH2Cl2 (0.5 M) at 0 C. The reaction mixture wasstirred at room temperature for 1 h. The solvent was removed under N2and the acid chloride (1 equiv) was dissolved in anhydrous CH2Cl2(0.5 M). The appropriate pyrazole (1.0 equiv) was dissolved in CH2Cl2(0.5 M) and cooled to 0 C. The acid chloride (1 equiv) in CH2Cl2 (0.5 M) was added dropwise and the reaction mixture was stirred atroom temperature for 3 h. The mixture was diluted with EtOAc, washedwith saturated aqueous NaCl, and dried over Na2SO4. Evaporationunder reduced pressure yielded the crude product that was purified byflash chromatography (SiO2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carbonitrile, and friends who are interested can also refer to it.

Reference:
Article; Otrubova, Katerina; Chatterjee, Shreyosree; Ghimire, Srijana; Cravatt, Benjamin F.; Boger, Dale L.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1693 – 1703;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

31108-57-3, name is 1H-Pyrazole-4-carbonitrile, 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. Quality Control of 1H-Pyrazole-4-carbonitrile

Prepared according General Procedure E, Step 2 from compound Cll (60 mg, 0.14 mmol) and lH-pyrazole-4-carbonitrile (63 mg, 0.67 mmol), with purification by column chromatography on silica gel to provide compound 27 as an off-white solid (27.3 mg, 44%): mp 176-178 C; 1HNMR (300 MHz, CDCI3) delta 7.83 (d, J = 12.3 Hz, 2H), 4.95 (q, J = 18.3 Hz, 2H), 3.53 (d, J = 9.0 Hz, IH), 3.33 (s, 3H), 3.22 (d, J = 9.0 Hz, IH), 2.59 (t, J = 9.3 Hz, IH), 2.26-1.35 (m, 17H), 1.31-1.08 (m, 9H), 0.66 (s, 3H) ppm; ESI MS m/z 437 [M+H-H2Of .

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

Reference:
Patent; SAGE THERAPEUTICS, INC.; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, Gerald; HERR, Robert, Jason; KARGBO, Robert, Borbo; WO2015/27227; (2015); 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. Safety of 1H-Pyrazole-4-carbonitrile

To a solution of 2-chloro-/V-(2,4-dimethoxybenzyl)-5-nitrobenzenesulfonamide (15.0 g, 38.8 mmol) in acetonitrile (450 mL) were added 1 /-/-pyrazole-4-carbonitrile (5.41 g, 93.1 mmol) and powdered potassium carbonate (16.1 g, 1 16 mmol) and it was stirred overnight at 100C. The reaction mixture was concentrated in vacuo and the residue was extracted with ethyl acetate and water. Pure title compound precipitated and was filtered off (9.09 g 20.5 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 (9.1 1 g., app. 60 % purity). (0390) LC-MS (Method B): Rt = 1 .17 min; MS (ESIneg): m/z = 442 [M-H]” (0391) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.53 (s, 3H), 3.64 (s, 3H), 4.08 (s, 2H), 6.20 (d, 1 H), 6.29 (dd, 1 H), 7.07 (d, 1 H), 7.89 (d, 1 H), 8.12 (br s, 1 H), 8.30 (br s, 1 H), 8.41 – 8.54 (m, 2H), 9.17 (br s, 1 H).

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

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; HAUFF, Peter; WERNER, Stefan; (94 pag.)WO2019/81573; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 31108-57-3

To a stirred solution of ethyl 2-((2-chloroethyl) amino)-2-phenylacetate (0.10 g, 0.413 mmol) in DMF (1 ml) was added K2C03 (0.114 g, 0.827 mmol) at 25 C. After stirring for 15 minutes, 1 /7-pyrazolc-4-carhonitrilc (0.046g, 0.496 mmol) was added at 25 C. The reaction mixture was heated at 60 C for 3 hours. Then the reaction mixture was poured into ice water (15 ml) and the product was extracted with ethyl acetate (2 x 30 ml). The combined organic layers were washed with brine (20 ml), dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford the title compound (0.050 g, 40%). LCMS: m/z = 299.76 [M+l].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; WILSON, Jonathan, E.; BRUCELLE, Francois; LEVELL, Julian, R.; (153 pag.)WO2019/161162; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 31108-57-3,Some common heterocyclic compound, 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, molecular formula is C4H3N3, 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.

Synthesis of III-B17 To a solution of III-B16 (90 mg, 0.2 mmol) and lH-pyrazole-4-carbonitrile (37.9 mg, 0.4 mmol) in acetone (5 mL) was added K2C03 (56.2 mg, 0.4 mmol). After stirring at 25C for 2 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 (0-30% of EtOAc in PE) and then by (1240) Prep-HPLC (Column: Waters Xbridge Prep OBD C18 150*30 5 pm; Condition: water (10 mM NH4HC03)-ACN; Begin B: 70; End B: 90; Gradient Time(min): 7; 100%B Hold (1241) Time(min): 1) to give III-B17 (32.6 mg, 53%) as a solid. 1H NMR (400 MHz, CDCl3) dH 7.86 (s, 1H), 7.81 (s, 1H), 5.04 (dd, J= 18.0, 95.6 Hz, 2H), 3.45-3.33 (m, 5H), 2.50 (t, J= 8.8 Hz, 1H), 2.40-2.23 (m, 2H), 1.88-1.10 (m, 23H), 1.00-0.83 (m, 1H), 0.60 (t, J= 7.6 Hz, 3H); LC-ELSD/MS purity 99%, MS ESI calcd. for C27H38N302 [M-H20+H]+ 436.3, found 436.3

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.; (276 pag.)WO2019/126741; (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.

General procedure: To a solution of II-M1 (510 mg, 1.19 mmol) in Acetone (10 mL) was added K2C03 (245 mg, 1.78 mmol) and 5-methyl-2H-tetrazole (211 mg, 1.42 mmol) at 20C. The mixture was stirred at 20C for 16 hrs. The reaction mixture was treated with water (20 mL). The mixture was extracted with EtOAc (2 x 20 mL). The combined organic phase was washed with brine (20 mL), dried over anhydrous Na2S04, filtered, concentrated in vacuum. The residue was purified by HPLC (Column: YMC-Actus Triart C18 l00*30mm*5um), gradient: 75-95% B (water (0.05%HCl)-ACN), flow rate: 25 mL/min) to afford the mixture II-M2 and II-M2a (Peak 1, 320 mg, ) as a solid and IJ~M2b (Peak 2, 50 mg, ) as a solid. (0920) The mixture II-M2 and II~M2a (320 mg, ) was purified by SFC (column: DAICEL (0921) CHIRALCEL OJ-H(250mm*30mm,5um)), gradient: 35-35% B (0. l%NH3H2O, B= EtOH ), flow rate: 200 mL/min) to afford II-M2 (Peak 1, 49 mg, 8 %) as a solid and II-M2a (Peak 2, 62 mg, 10 %) as a solid. (0922) The residue II-M2b (50 mg, ) was dissolved in MeCN (5 mL) at 25C and concentrated in vacuum to II~M2b (45 mg, 8 %) as a solid.

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.; (276 pag.)WO2019/126741; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31108-57-3, name is 1H-Pyrazole-4-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 31108-57-3, Computed Properties of C4H3N3

In a nitrogen-purged glove box, (oxybis(2,1-phenylene))bis(diphenylphosphine) (1.0 g, 1.86 mmol) and toluene (20 mL) were added to a glass jar, containing a TEFLON coated stir bar. A solution of mesitylcopper(I) (0.34 g, 1.86 mmol), in toluene (10 mL), was then added, while stirring. After a few minutes, 4-cyanopyrazole (0.17 g, 1.81 mmol) was added, the jar was capped, and the resulting mixture was stirred at 60C for 3 hours. After cooling to room temperature, the milky white mixture was concentrated, and further dried under vacuum for one hour at 110C. The resulting white solid (0.78 g) was isolated. A PMMA film of this complex did not show emission upon UV-excitation.

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; DOW GLOBAL TECHNOLOGIES LLC; LAITAR, David S.; CLARK, Thomas P.; RACHFORD, Aaron A.; MUKHOPADHYAY, Sukrit; DE VRIES, Timothy S.; DEVORE, David D.; (31 pag.)WO2016/57441; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics