Category: 25016-11-9

Application of 25016-11-9, 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 25016-11-9 as follows.

Potassium terf-butoxide (23.47 g of 95%, 199.1 mmol, 2.44 equiv.) was suspended in anhydrous DME (90 mL) and cooled to – 60 0C. TosMIC (23.76 g, 121.7 mmol, 1.49 equiv.) was dissolved in anhydrous DME (75 mL), and this was added drop-wise to the potassium terf-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55 0C, the compound of formula IX, in anhydrous DME (55 ml_), was added over 23 minutes. The reaction was stirred one hour at – 55 to – 50 0C to yield a thick suspension. Methanol (90 ml_) was then added resulting in a clear brown solution. The cooling bath was removed, and after stirring 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85 0C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 ml_) with acetic acid (9 ml_). This was extracted with ethyl acetate (3 x 250 ml_), and these extracts were combined, washed with saturated aqueous sodium chloride (100 ml_), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield the compound of formula Xl as a bright yellow oil (7.89 g, 63% yield).

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; WO2008/153870; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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: C5H6N2O

Preparation 65: 3 ‘-Chloro-4-( 1 -methyl- 1 H-pyrazol-4-ylmethyl)-3 ,4,5 ,6-tetrahydro-2H- [l,2′]bipyrazineDissolve 3′-chloro-3,4,5,6-tetrahydro-2H-[l,2’]bipyrazinyl (3.43 g, 17.3 mmol) in tetrahydrofuran (100 mL). Add 1 -methyl- lH-pyrazole-4-carbaldehyde (2.244 g, 20.38 mmol) in dry tetrahydrofuran (5 mL), stir for 10 min. at room temperature, add sodium triacetoxyborohydride (4.32 g, 20.4 mmol) and subject the reaction to ultrasound stirring for 6 hr. at room temperature. Add saturated aqueous sodium hydrogen carbonate (100 mL) then 2 N sodium hydroxide (10 mL) to the mixture and extract with DCM (2 x 200 mL). Pass the combined DCM extracts through an 1ST Phase Separator Frit, concentrate and purify (silica gel chromatography, eluting with 0: 100 to 8:92 methanol:DCM), to give the title preparation as a crystalline solid (5.21 g, 92%). MS (ES): m/z = 293.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 1-Methyl-1H-pyrazole-4-carbaldehyde

1-methyl-1H-pyrazole-4-carbaldehyde previously obtained, malonic acid (4.68g, 45mmol), pyridine (4ml, 50mmol) and piperidine (0.09ml, 1mmol) were placed in a 250 ml flask and heated at 110C for 6h under nitrogen, then the reaction was stopped and cooled. The resulting solution was added with water (100ml), followed by addition of strong aqua dropwise to dissolve all the solids. The solution was then brought to pH~1 with concentrated hydrochloric acid. The precipitate thus obtained was collected by filtration, washed with water several times and then dried in vacuo to give the title compound (2.9g). 1H-NMR (d6-DMSO, 300 MHz) delta3.83 (s, 3H), 6.17 (d, 1H, J=16.2), 7.45 (d, 1H, J=15.9), 7.83 (s, 1H), 8.07 (s, 1H), 12.07 (s, 1H).

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; WANG, Kai; EP2725024; (2014); 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C5H6N2O

Step 2: 1 – methyl – l H-pyrazole-4-carbaldehyde oxime A mixture of the combined organic layer having 1 -methyl- l H-pyrazole-4-carbaldehyde and ethyl acetate obtained from step 1 , hydroxylamine hydrochloride (63.48 gm, 0.9135 moles) were refluxed at 70-80C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5C, to this added DM water ( 100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5C. The reaction mixture was stirred for 10 min at 20-30C. The organic layer was separated and aqueous layer was extracted with ethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 min and separated the final aqueous layer and organic layer. The organic layer was evaporated to obtain the 1 -methyl- lH-pyrazole-4- carbaldehyde oxime. Dry wt : 60 gm Yield : 1.2 w/w (79%) HPLC purity : 99.78%

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 25016-11-9.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2111; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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 25016-11-9, COA of Formula: C5H6N2O

A solution of 1-methyl-1H-pyrazole-4-carbaldehyde (2.73 g, 24.80 mmol), (R)-2-methyl-2-propanesulfinamide (3.30 g, 27.30 mmol), and Ti(OiPr)4 (35.2 g, 37.1 mL, 0.124 mol) in THF (60 mL) was stirred with heating on a water bath at 50 C for 20 h. The resulting mixture was poured into water (100 mL) with stirring for 15 min, then filtered and the precipitate was washed twice with DCM. The filtrate was diluted with water (100 mL) and extracted with DCM (20 mL * 3). The combined extracts were dried over K2CO3, filtered through the pad of silica gel, and evaporated under reduced pressure and dried in vacuo to afford pure 2b 5.16 g (97%). = -130.7 (c 1, CHCl3), 1H NMR (400 MHz, CDCl3): delta 8.41 (s, 1H, CH=N), 7.83 (s, 1H, CHpyr), 7.78 (s, 1H, CHpyr), 3.89 (s, 3H, Me), 1.15 (s, 9H, tBu). 13C NMR (100 MHz, CDCl3): delta 154.28, 139.91, 132.14, 119.86, 57.30, 39.29, 22.39 3C. MS (70 eV, EI): m/z (%) = 214 (60) [MH]+, 157 (100), 130 (10), 109 (56), 108 (48), 83 (18), 82 (20), 81 (8), 41 (7). C9H15N3OS (213.3): calcd C 50.68, H 7.09, N 19.70, S 15.03, found C 50.42, H 7.11, N 19.55, S 14.88.

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, 1-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kuznetsov, Nikolai Yu.; Khrustalev, Victor N.; Strelkova, Tatyana V.; Bubnov, Yuri N.; Tetrahedron Asymmetry; vol. 25; 8; (2014); p. 667 – 676;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, molecular formula is C5H6N2O, 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-carbaldehyde

Step 2) Potassium t-butoxide (23.47 g, 199.1 mmol, 2.44 eq.) was suspended in anhydrous DME (90 mL) and cooled to – 60C. Tosyl methyl isocyanide (23.76 g, 121.7 mmol, 1.49 eq.) was dissolved in anhydrous DME (75 mL) and the solution was added drop- wise to the potassium t-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55C, the aldehyde from Step 1 in anhydrous DME (55 mL) was added over 23 minutes. The reaction was stirred for one hour at – 55 to – 50C, and then methanol (90 mL) was added. The cooling bath was removed, and after stirring for 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 mL) with acetic acid (9 mL). This was extracted with ethyl acetate (3 x 250 mL), and these extracts were combined, washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield a bright yellow oil in 63% yield (7.89 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHUMWAY, Stuart Denham; TONIATTI, Carlo; ROBERTS, Brian Scott; MARTIN, Melissa M.; WO2013/39854; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 25016-11-9, 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

1-Methyl-1H-pyrazole-4-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (6.0 g, 0.04 mol) and 50 g of acetic acid (0.83 mol) were mixed at room temperature. Add 12.5 g of ammonia-containing molecular mass concentration of 25% ammonia water and 100 ml of water. heating to 90 C, the reaction is exothermic, maintaining the reaction temperature of 100 C, refluxing reaction for 1 hour (to 1-methyl-1H-pyrazole-4-carbaldehyde reaction is complete), The reaction solution was cooled to room temperature, poured into ice water and quenched and diluted. neutralize until the reaction solution is neutral, extract with ethyl acetate, and dry. After concentrating the product, it is distilled under reduced pressure and recrystallized.The product obtained was 10.2 g, the yield was 95%, and the purity was over 99%.

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-11-9, The chemical industry reduces the impact on the environment during synthesis 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: 4-(2,3-diamino-5-chloropyridin-4-ylamino)-l,7,7-trimethylbicyclo[2.2.1]heptan-2-one (10) (380mg, 1.23mmol), 1 -methyl- lH-pyrazole-4-carbaldehyde (135mg, 1.23mmol) were taken in EtOH (15ml) to which ammonium acetate (112mg) was added and the reaction mixture was heated at 70C for 48h. Crude LCMS showed the desired product along with trace of starting material. The reaction mixture was allowed to come to rt and the precipitated was filtered and washed well with ethanol to afford the desired product (478mg, 25%) as an off white solid. NMR: delta (, 400M Hz, DMSO-d6): 0.90 (3 H, s), 0.91 (3 H, s), 1.09 (3 H, s), 1.40 – 1.80 (3 H, m), 2.30 – 2.60 (1 H, m), 3.00 – 3.10 (1 H, m), 3.51 – 3.70 (1 H, m), 3.93 (3 H, s), 5.36 (1 H, s), 8.00 (1 H, s), 8.04 (1 H, s), 8.31 (1 H, s), 13.09 (1 H, s). LCMS (254nm): [M+H] + 399.00 (96.43 %). HPLC: 254 nm (94.06 %)

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, 1-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPHALON, INC.; BRESLIN, Henry J.; CURRY, Matthew A.; GINGRICH, Diane E.; LEARN, Keith S.; OTT, Gregory R.; WAGNER, Jason C.; WO2013/116291; (2013); 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

Step 2:, I-methyl -IH-pyrazole-4-carbaldehyde oxirne VA mixture Of the combined organic layer having l-methyl-IH-pyrazole-4-carbaldehyde and ethyl acetate obtained from step I and hydroxylamine hydrochloride (63.48gm, 0.9135 moles) was refluxed at 70-80C for 2-4 hours. The progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 0-5C, to this added DM water (100 ml) and 25% aqueous ammonia solution (100 ml) at 0-5C. The reaction mixture was stirred for 10 mm at 20-30C. The organic layer was separated and aqueous layer was extracted withethyl acetate (250 ml). The entire organic layer was transferred to the reaction vessel and washed with 10% brine solution (500 ml). Stirred for 10 mm and separated the final aqueouslayr and organic layer. The organic layer was evaporated to obtain the l-methyl-lHpyrazole-4-carbaldehyde oxime.Drywt V : 60gmYield :1.2w/w(79%)HPLC purity : 99.78%

The synthetic route of 25016-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2110; (2014); 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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Safety of 1-Methyl-1H-pyrazole-4-carbaldehyde

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (5.4 g, 22.7 mmol, 1 eq) in THF (100 mL) at 0C was added sodium hydride (60 % in mineral oil, 1.2 g, 29.5 mmol, 1.3 eq)portion-wise and the mixture was allowed to stir at the same temperature for 30 minutes. To this mixture was added a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (2.5 g, 22.7 mmol, 1.0 eq) in THF (10 mL) and the resulting mixture was allowed to stir at 0 C for 1 h. Progress of reaction was monitored by TLC. After completion, reaction mixture was diluted with saturated aq. NH4C1 (100 mL) and extracted with ethyl acetate (3 x 100 mL). Combined organic layer waswashed with brine, dried over anhydrous Na2SO4 and evaporated to dryness under vacuum to afford ethyl (E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate (3.9 g, 95 %) which was used in the next step without further purification.

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; AURANSA INC.; PROTTER, Andrew, Asher; GREEN, Michael, John; CHANG, Hak, Jin; PHAM, Son, Minh; CHAKRAVARTY, Sarvajit; LUEDTKE, Gregory, R.; (254 pag.)WO2019/103897; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics