Tag: M.W:100-200

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 1203705-55-8 as follows. Safety of 3-Bromo-1H-pyrazol-5-amine

1-(1,3-dimethyl-1H-pyrazol-4-yl)-4,4,4-trifluoro-3-hydroxybut-2-en-1-one (Preparation 5, 1.7 g) and 3-bromo-1H-pyrazol-5-amine (Preparation 6, 1.18 g) in Acetic acid (52.61 mL) was heated at 120 C. in a sealed tube overnight. The reaction solution was cooled to room temperature, and poured into ice water (500 mL) resulting in a white precipitate. The precipitate was filtered and washed with copious amounts of water. The precipitate was then collected and dried in vacuo to afford the title compound as a white powder (1.9 g, 73.1%). [0524] 1HNMR (400 MHz, DMSO-d6) delta: 2.47 (s, 3H), 3.79, (s, 3H), 6.95, (s, 1H), 7.73, (s, 1H), 8.67, (s, 1H).

According to the analysis of related databases, 1203705-55-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boivin, Roch; Carlson, Eric; Endo, Atsushi; Hansen, Hans; Hawkins, Lynn D.; Ishizaka, Sally; Mackey, Matthew; Narayan, Sridhar; Satoh, Takashi; Schiller, Shawn; US2013/324547; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 4149-06-8, These common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, 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.

A solution of 3-amino-1-phenyl-2-pyrazolin-5-one 1 (0.35 g, 2 mmol), dimedone 2 (0.28 g, 2 mmol), aldehyde 3 (0.28 mg, 2 mmol) and Cell-LA-TEA+/Fe3O4 nanocatalyst (0.03 g, 0.09 mol%) in H2O/EtOH (3:2) was subjected to ultrasonic irradiation (ultrasonic bath, room temperature). The progress of the reaction was controlled by TLC (hexane/ethyl acetate, 2:3). After reaction completion, the nanocatalyst was separated magnetically from the reaction mixture and used for subsequent cycles after washing with ethanol. By cooling the reaction solution, the solid product was collected, separated and recrystallized from methanol to get the pure product.

Statistics shows that 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one is playing an increasingly important role. we look forward to future research findings about 4149-06-8.

Reference:
Article; Zahedifar, Mahboobeh; Pouramiri, Behjat; Razavi, Razieh; Research on Chemical Intermediates; vol. 46; 5; (2020); p. 2749 – 2765;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34334-96-8, name is 3-Methyl-5-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 34334-96-8, Formula: C4H5N3O2

A solution of 5-methyl-3-nitro-lH-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, 1 1.6 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-lH-pyrazol-l-yl)ethanol as a white solid: NMR (400 MHz, DMSO-i¾d 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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-5-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; BLOMGREN, Peter; CURRIE, Kevin, S; KROPF, Jeffrey, E.; LEE, Seung, H.; MITCHELL, Scott, A.; SCHMITT, Aaron, C.; XU, Jianjun; ZHAO, Zhongdong; WO2011/112995; (2011); 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. 473528-88-0, name is 4-Bromo-1-methyl-1H-pyrazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 473528-88-0

To a mixture of OI-5b (700 mg, 3.72 mmol, 1.0 eq), 4a-1 (1.27 g, 4.09 mmol, 1.1 eq), DPPF (42 mg, 0.503 mmol, 0.1 eq) and DIEA (942 mg, 7.55 mmol, 1.5 eq) in toluene (10 mL) was added Pd(dba)2 (150 mg, 0.260 mmol, 0.07 eq) under nitrogen atmosphere. The mixture was stirred at 110 C. for 16 h. Then the mixture was filtered and extracted with water and ethyl acetate. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford OI-5c (120 mg, 10%)

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; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1613191-73-3, 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 1613191-73-3 as follows.

Step 2: 2-amino- 7-(tert-butoxycarbonyl)-5, 6, 7, 8-tetrahydropyrazolo[ 1, 5-a]pyrido[ 4, 3- dJpyrimidine-3-carboxyiic acid 5 [00269] A mixture of tert-butyl 3-(l,3-dioxolan-2-yl)-4-oxo-piperidine-l-carboxylate (4.3 g, 15.85 mmol), allyl 3,5-diamino-lH-pyrazole-4-carboxylate 3 (2.888 g, 15.85 mmol), KOH (215.1 mg, 3.833 mmol) in dioxane (86 mL) was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in DCM (50 mL). Phenylsilane (1.715 g, 1.953 mL, 15.85 mmol) and palladium triphenylphosphane (549.5 mg, 0.4755 mmol) were added to the reaction mixture which was stirred at RT for 4 h. The precipitate was filtered off and washed with DCM yielding 2-amino-7-(tert-butoxycarbonyl)-5,6,7,8- tetrahydropyrazolo[l,5-a]pyrido[4,3-d]pyrimidine-3-carboxylic acid 5 as a beige solid which was used in next step without further purification. MS (ES+) 334.1.

According to the analysis of related databases, 1613191-73-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 4.07 g, 32.2 mmol), DIEA (12.2 g, 94.1 mmol) in CH2Cl2 (30 mL) was added EDCI (10.3 g, 53.7 mmol) and DMAP (3.94 g, 32.2 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min under N2. Then 4-bromo-2-methylaniline (compound 7, 5.00 g, 26.9 mmol) was added, the mixture was stirred at -5 C. for 30 min, then warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.27) showed one new point formed. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatography (petroleum ether: ethyl acetate=80:20 to 50:50) to give N-(4-bromo-2-methylphenyl)-1-methyl-1H-pyrazole-5-carboxamide (compound 8, 6.40 g, 81% yield) as light yellow solid. 1H NMR (400 MHz, CDCl3) delta delta ppm 7.72 (d, J=8.2 Hz, 1H), 7.47-7.58 (m, 2H), 7.33-7.41 (m, 2H), 6.64 (s, 1H), 4.20 (s, 3H), 2.28 (s, 3H); ES-LCMS m/z 294.1 [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 1-Methyl-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 2644-93-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde, 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. category: pyrazoles-derivatives

To a flask containing 6-bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline (1.37 g, 3.86 mmol, Intermediate 10: step d) was added THF (45 mL) at room temperature which resulted in a colorless homogeneous mixture. The solution was cooled to -78 C. and then n-BuLi (2.5 M in hexanes, 1.8 mL, 4.5 mmol) was added dropwise. The color of the solution became a reddish-brown color. After 4 minutes, 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (300 mg, 2.17 mmol, in 3 mL THF) was introduced and the color of the mixture changed from reddish-brown to a yellow-greenish color over 5 minutes. The mixture was allowed to warm to 0 C. over 45 minutes at which time the reaction was quenched with aqueous NH4Cl solution. The mixture was diluted further with water and extracted with EtOAc (3*150 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a light orange foam. FCC on silica gel (2% MeOH-DCM increasing to 8% MeOH-DCM) afforded the title compound as a light yellow amorphous solid. 1H NMR (500 MHz, CDCl3) delta ppm 8.23 (s, 1H), 7.78 (d, J=8.6 Hz, 1H), 7.56-7.47 (m, 3H), 7.40 (d, J=8.1 Hz, 2H), 6.01 (d, J=3.0 Hz, 1H), 4.35 (s, 2H), 4.06 (s, 3H), 3.70 (s, 3H), 2.14 (s, 3H), 2.12 (s, 3H), 2.09 (d, J=3.3 Hz, 1H). MS (ESI): mass calcd. for C25H23ClF3N3O2, 489.1; m/z found, 490.1 [M+H]+.

The synthetic route of 1,3,5-Trimethyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; US2015/105372; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 16617-46-2,Some common heterocyclic compound, 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, molecular formula is C4H4N4, 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.

5-Amino-1H-pyrazole-4-carbonitrile (1) (5 g, 0.046 mol) was added to cooled concentrated sulphuric acid (10 ml) with stirring sothat the temperature did not rise above 20 °C. The addition took about one-half hour and solution was stirred at room temperaturefor 4 h. The acid solution was then poured with stirring into ice and the solution was kept overnight in the refrigerator. The solid was then filtered and washed with water to free of excess sulphuric acid to afford the desired product 5-amino-1H-pyrazole-4-carboxylic acid amide (2) as white solid; (5.19 g, 89percent); mp 220-222 °C (Lit.mp 222-225 °C) [33].

The synthetic route of 16617-46-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singla, Prinka; Luxami, Vijay; Singh, Raja; Tandon, Vibha; Paul, Kamaldeep; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 24 – 35;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 4149-06-8, 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. 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

The chemical industry reduces the impact on the environment during synthesis 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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. 1310350-99-2, name is 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Chloro-1-(difluoromethyl)-1H-pyrazole-3-carboxylic acid

A solution of 4-chloro-1-difluoromethyl-1H-pyrazole-3-carboxylic acid (150 mg, 0.76 mmole) in dichloromethane (5 ml) was subsequently treated at 22 C. with N,O-dimethylhydroxylamine hydrochloride (78 mg, 0.80 mmole), N-methylmorpholine (0.09 ml, 0.8 mmole) and EDCI.HCl (154 mg, 0.8 mmole) and stirring was continued for 16 h. The mixture was washed with 1 M aqueous HCl and H2O, the organic layer was dried, evaporated and the residue purified by chromatography on silica gel using cyclohexane/AcOEt (2:1) to give the title compound (164 mg) as a colorless oil. MS: m/z=240.1 [M]+.

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; Banner, David; Gabellieri, Emanuele; Guba, Wolfgang; Hilpert, Hans; Hornsperger, Benoit; Humm, Roland; Mauser, Harald; Mayweg, Alexander V.; Narquizian, Robert; Pinard, Emmanuel; Rogers-Evans, Mark; Woltering, Thomas; Wostl, Wolfgang; US2012/35195; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics