Day: May 14, 2021

1072-91-9, name is 1,3,5-Trimethylpyrazole, 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. Application In Synthesis of 1,3,5-Trimethylpyrazole

General procedure: SOCl2 (5 mL) was added to a round-bottom flask, and then 1a-i(1.0 mmol) and a catalytic amount of DMF (0.1 mmol) were added. Themixture was heated to reflux for 4 h (reaction monitored by HPLC),then excess SOCl2 was evaporated under reduced pressure. The residuewas dispersed in H2O (200 mL) and extracted with AcOEt. The organicphase was separated, dried, and concentrated. It was then purified byflash column chromatography (eluent: ethyl acetate/petroleum ether,1 : 10 v/v) to afford 2a-i.

The synthetic route of 1072-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yi; Liu, Yuanyuan; Xu, Guanghui; Chen, Kai; He, Guangke; Huang, Bin; Journal of Chemical Research; vol. 38; 11; (2014); p. 658 – 661;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 139756-04-0 as follows. Product Details of 139756-04-0

(Step a) Preparation of 4-[2-Propoxy-5-(Chlorosulfonyl)Benzamido]-1-Methyl-3-Propyl-5-Carbamoyl Pyrazole To 23 ml of chlorosulfonic acid cooled to 0 C., 10 g of 4-[2-propoxy benzamido]-1-methyl-3-propyl-5-carbamoyl pyrazole was added and then stirred at room temperature for 2 hours. Reaction mixture was added to ice water of 0 C. and then stirred for 1 hour to obtain white solid, which was filtered and washed with water. The obtained white solid was dissolved in ethyl acetate. The solution was successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product and triturated with hexane to give 9.14 g of the title compound. 1H NMR (CDCl3): 0.92(t,3H), 1.08(t,3H), 1.62(m,2H), 1.97(m,2H), 2.50(t, 2H), 4.04(s,3H), 4.32(t,2H), 5.63(br s,1H), 7.24(d,1H), 7.54(br s, 1H), 8.15(dd,1H), 8.93(d,1H), 9.17(br s,1H)

According to the analysis of related databases, 139756-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yoo, Moo-Hi; Kim, Won-Bae; Chang, Min-Sun; Kim, Soon-Hoe; Kim, Dong-Sung; Bae, Chul-Jun; Kim, Yong-Duck; Kim, Eun-Ha; US2003/176696; (2003); 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. 75092-25-0, name is Methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a mixture of methyl 4-iodo-1-methyl-1H-pyrazole-3-carboxylate(29; 263 mg, 0.99 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (30; 1.01 g, 4.94 mmol) in DMF(3.4 mL) and H2O (1.0 mL) were added Cs2CO3 (644 mg, 1.98 mmol) and Pd(PPh3)4 (571 mg, 0.49 mmol), and the mixture was stirred at 80 C for 3 h. After the mixture was cooled at room temperature, the mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (0-100% EtOAc inCHCl3) to give 31 (87 mg, 41%) a pale yellow oil. 1H NMR (DMSOd6) d 3.77 (s, 3H), 3.95 (s, 3H), 7.49 (d, 2H, J = 5.3 Hz), 8.22 (s,1H), 8.55 (d, 2H, J = 5.3 Hz); MS (ESI) m/z 218 [M+H]+.

According to the analysis of related databases, 75092-25-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Narazaki, Fumie; Shiina, Yasuhiro; Seo, Ryushi; Amano, Yasushi; Mihara, Takuma; Moriguchi, Hiroyuki; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3351 – 3367;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 948571-47-9, name is 2-(4-Amino-1H-pyrazol-1-yl)ethanol, molecular formula is C5H9N3O, 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 2-(4-Amino-1H-pyrazol-1-yl)ethanol

General procedure: A solution of compound 1 (0.15 mmol), 2 (0.1 mmol) and Et3N (20 mmol%) in DCM (1.0 mL) was reacted at room temperature for appropriate times (monitored by TLC). After removal of the solvent under reduced pressure, the crude product was purified directly by column chromatography on silica gel (hexanes/EtOAc=5/1-2/1) to afford the desired products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 948571-47-9, its application will become more common.

Reference:
Article; Wang, Xiao-Wei; Li, Peng; Xiao, Hua; Zhu, Shi-Zheng; Zhao, Gang; Tetrahedron; vol. 67; 39; (2011); p. 7618 – 7621;,
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. 916766-83-1, name is 3-(4-(Chloromethyl)phenyl)-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 916766-83-1

4 -Chloro-5-methyl-6-(l-methyl-lH-pyrazol-3-yl)picolinonitrile (119 mg, 0.52 mmol, 1 eq), bis(pinacolato)diboron (259 mg, 1.02 mmol, 2 eq), potassium acetate (200 mg, 2.04 mmol, 4 eq), and Pd(dppf)Cl2 DCM (42 mg, 0.051 mmol, 0.1 eq) were charged to a vial which was sealed and evacuated under vacuum and purged with N2. l,4-dioxane (5 mL) was then added via syringe, and the resulting solution was stirred at 90 C for 6 h, after which time an additional 1 eq bis(pinacolato)diboron, 1 eq potassium acetate, and 0.025 eq Pd(dppf)Cl2 DCM were added. The resulting solution was stirred at 90 C for 16 h, after which time the reaction mixture was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure to give the pinacol ester intermediate (v) as a brown solid which was used directly without further purification (166 mg, 100%). ES-MS [M+H]+ = 243.2 (mass of free boronic acid is observed). To a vial containing crude pinacol ester (166 mg, 0.52 mmol, 1 eq), 3-[4-(chloromethyl)phenyl]-l-methyl-pyrazole (169 mg, 0.82 mmol, 1.6 eq), cesium carbonate (502 mg, 1.53 mmol, 3 eq) and Pd(dppf)Cl2 DCM (56 mg, 0.077 mmol, 0.15 eq) were added. The vial was sealed and evacuated under vacuum and purged with N2. 5: 1 1,4- dioxane/EEO solution (4 mL total, degassed) was then added via syringe and the resulting solution was stirred at 90 C for 3 h, after which time the reaction mixture was cooled to r.t. and filtered through a plug of Celite with EtOAc and DCM. Solvents were concentrated under reduced pressure, and crude residue was purified by column chromatography (5-100% EtOAc in hexanes) to give the title compound as a slightly yellow foamy solid (126 mg, 67%). MR (400 MHz, CDCh) d 7.76 (d, J= 8.1 Hz, 2H), 7.43 (s, 1H), 7.38 (d, J= 1.8 Hz, 1H), 7.32 (s, 1H), 7.14 (d, J= 8.0, 2H), 6.75 (s, 1H), 6.53 (d, J= 1.8 Hz, 1H), 4.07 (s, 2H), 3.98 (s, 3H), 3.96 (s, 3H), 2.59 (s, 3H). ES-MS [M+H]+ = 369.2.

The synthetic route of 916766-83-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; LINDSLEY, Craig W.; CONN, P. Jeffrey; ENGERS, Darren W.; ENGERS, Julie L.; BENDER, Aaron M.; LONG, Madeline; (120 pag.)WO2019/241467; (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. 107862-65-7, name is 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole, A new synthetic method of this compound is introduced below., Safety of 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole

To a solution of 5,6-dihydro-4H-pyrrolo[l ,2-Z?]pyrazole (47.2 g, 437 mmol) and sodium acetate (36.2 g, 440 mmol) in acetic acid (750 mL) at 0C was added bromine (22.4 mL, 435 mmol). After 10 minutes, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (5 x 200 mL). The organic layers were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford 3-bromo-5,6-dihydro-4H-pyrrolo[l,2-6]pyrazole.

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; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; BIENSTOCK, Corey, E.; BUTCHER, John, W.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; HAIDLE, Andrew, M.; JEWELL, James, P.; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETERSON, Scott, L.; SMITH, Graham Frank; WO2013/52394; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 75092-30-7, 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. 75092-30-7, name is 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of Preparation 16 (50 mg, 0.0897 mmol), 4-iodo-2-methyl-2H-pyrazole-3-carboxylic acid (MFCD00461121) (23 mg, 0.0897 mmol), CS2CO3 (58 mg, 0.179 mmol) and PdCl2(dppf)2.CH2Cl2 (4 mg, 0.00448 mmoL) in 1,4-dioxane (0.8 mL) and H2O (0.2 mL) was stirred at 80 C. for 16 h. LCMS showed the reaction was complete. The reaction was dried over Na2SO4 and filtered. The filtrate was concentrated to dryness and purified by prep-HPLC (petroleum ether:EtOAc, 1:1) to give the N-BOC intermediate (10 mg, 20%) as a white solid. The reaction was repeated to obtain additional material.

The chemical industry reduces the impact on the environment during synthesis 4-Iodo-1-methyl-1H-pyrazole-5-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; Darout, Etzer; Dullea, Robert; Hawkins, Julie Jia Li; Londregan, Allyn T.; Loria, Paula M.; Maguire, Bruce; McClure, Kim F.; Petersen, Donna N.; Piotrowski, David W.; US2014/315928; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 139756-04-0, name is 1-Methyl-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide, 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 139756-04-0, Recommanded Product: 139756-04-0

3) 1-methyl-3-propyl-5 – (2-propoxy-phenyl) – 1,6-dihydro -7H-pyrazolo-[ 4,3-d] pyrimidin-7-one preparation: heating 6mmol compound 1-methyl-3-propyl-4 – (2-propoxy benzamido- ) pyrazole-5-carboxamide dissolved in 40 ml volume ratio (20-80): 1 ethanol in a mixture with hydrogen peroxide, add 6mmol naoh, stirring to dissolve, microwave heating 120 C reaction 25 minutes, after the reaction of the organic solvent is removed by reduced pressure distillation, the residue is distilled water washes, ethyl acetate extraction, organic subtraction-pressure distillation to remove the solvent, dried to obtain 1-methyl-3-propyl-5 – (2-propoxy-phenyl) – 1,6-dihydro -7H-pyrazolo-[ 4,3-d] pyrimidin-7-one, yield 85-90%;

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-4-(2-propoxybenzamido)-3-propyl-1H-pyrazole-5-carboxamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Pharmaceutical University; CHEN, SIDONG; WANG, BAOGUO; MEI, WENJIE; ZHOU, JUNLI; JI, HENG; (20 pag.)CN103755709; (2016); B;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 873191-23-2,Some common heterocyclic compound, 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, molecular formula is C6H9BrN2, 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.

BEMP (137 mul_, 0.47 mmol) is added to a solution of (2-methyl-1/-/-pyrrolo[2,3- 6]pyridin-3-yl)-acetic acid methyl ester (60 mg, 0.29 mmol) in DMF (0.8 ml_). After 35 minutes, the diethyl ether layer from Step 71a (1.8 mL) is added. After 3 days, the reaction is partitioned between water and 1 :1 EtOAc/ether. The organic layer is washed with brine then evaporated. The residue is purified by flash column chromatography (49:1 EtOAc/MeOH elution) to furnish [1-(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-2-methyl-1/-/- pyrrolo[2,3-/)]pyridin-3-yl]-acetic acid methyl ester; MH+ = 313.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/68418; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1239363-40-6, The chemical industry reduces the impact on the environment during synthesis 1239363-40-6, name is 1-Cyclopropyl-4-iodo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Into a dry microwave vial with stir bar was added intermediate 15.2 (200 mg, 0.625 mmol), potassium phosphate tribasic (398 mg, 1.876 mmol), (Irans)-N 1 N2-dimethylcyclohe xane-l, 2-diamine (44.5 mg, 0.313 mmol), l-cyclopropyl-4-iodo-lH-pyraz ole (293 mg, 1.251 mmol), and copper(I) iodide (35.7 mg, 0.188 mmol). The vial was sealed and purged with nitrogen. Then, DMSO (3.5 mL) was added and the solution was heated to 80C overnight. The next day, the crude material was filtered through a plug of Celite (diatomaceous earth) using EtOAc. The filtrate was concentrated and purified by reverse phase prep-HPLC (Method A) to afford intermediate 15.3, (R and S)-5-chloro-l-(l -cyclopropyl- lH-pyrazol-4-yl)-6- (l-(3-methyltetrahydrofuran-3-yl)piperidin-4-yl)-lH-indazole, TFA salt. MS (ESI) m/z calc?d for C23H28CIN5O [M+H]+ 426, found 426.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics