Day: June 30, 2021

Related Products of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 2,4,6-trichloropyrimidine (Alfa, 12.25 g, 66.8 mmol), 3-amino-5- cyclopropyl-lH-pyrazole (Fluorochem 8.23 g, 66.8 mmol) and triethylamine (11.2 mL, 80.4 mmol) in ethanol (100 mL) was stirred at room temperature for 16 hours under Ar (balloon). The solvent was removed in vacuo and the crude material was dissolved in ethyl acetate. The solution was washed with water and dried (Na2S04), filtered and evaporated to give a beige solid. Pure product was obtained as a white crystalline solid afterrecrystallisation from acetonitrile. It was possible to obtain a second crop. From two runs performed under the same conditions, 29.0 g (88%) of 2,6-dichloro-N-(5-cyclopropyl-lH- pyrazol-3-yl)pyrimidin-4-amine. The product contained -10 % acetonitrile but was carried through to the next step regardless.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BANDYOPADHYAY, Deepak; EIDAM, Patrick M.; GOUGH, Peter J.; HARRIS, Philip Anthony; JEONG, Jae U.; KANG, Jianxing; KING, Bryan Wayne; LAKDAWALA SHAH, Ami; MARQUIS, JR., Robert W.; LEISTER, Lara Kathryn; RAHMAN, Attiq; RAMANJULU, Joshi M.; SEHON, Clark A; SINGHAUS, JR., Robert; ZHANG, Daohua; WO2014/125444; (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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Safety of 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Example 6 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid chloride 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid obtained by example 5 is treated with oxalyl chloride (1,25 eq) in toluene, and a few drops of dimethylformamide are added. The mixture is concentrated under reduced pressure to yield the carboxyl chloride.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; JAUNZEMS, Janis; (39 pag.)WO2019/122164; (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. 127107-23-7, name is 1-Methyl-1H-pyrazol-4-amine hydrochloride, A new synthetic method of this compound is introduced below., name: 1-Methyl-1H-pyrazol-4-amine hydrochloride

HATU (0.329 g, 0.867 mmol), DBU (0.152 g, 1.000 mmol) and 1- methyl-lH-pyrazol-4-amine hydrochloride (0.0745 mL, 0.800 mmol) were added to 6- bromoquinazolin-4(3H)-one (0.150 g, 0.667 mmol) in MeCN (3.5 mL). The solution was aged for 25 hours at ambient temperature before it was diluted with EtOAc and washed with brine-water. The concentrated organics were purified via silica gel chromatography eluting with 2% MeOH-EtOAc to yield 6-bromo-3-(l-methyl-lH-pyrazol-4-yl)quinazolin-4(3H)-one (0.018 g, 0.059 mmol, 18% yield).

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; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRINA, Jonas; HANSEN, Joshua D.; LAIRD, Ellen; MATHIEU, Simon; MORENO, David; REN, Li; RUDOLPH, Joachim; WENGLOWSKY, Steven Mark; WO2012/118492; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1453-58-3, 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 1453-58-3 as follows.

To a solution of 3-methyl-1H-pyrazole (10.99 g, 134 mmol) in N,N-dimethylformamide (100 ml) at 0° C. was added sodium hydride (3.71 g, 154 mmol, 60percent dispersion). The reaction was stirred at 0° C. for 2 hours. 3-Fluoropyridine (10.0 g, 103 mmol) was added, and the reaction was stirred at 100° C. overnight. The reaction was cooled to room temperature and water was added slowly. The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, concentrated and chromatographed (0-100percent ethyl acetate/hexanes) to afford 3-(3-methyl-1H-pyrazol-1-yl)pyridine (8.4 g, 52.77 mmol, 51.2percent) and 3-(5-methyl-1H-pyrazol-1-yl)pyridine (1.0 g, 6percent). Analytical data of both products is consistent with that reported under Example 6, Step 1.

According to the analysis of related databases, 1453-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow Agrosciences LLC; Niyaz, Noormohamed M.; Garizi, Negar; Zhang, Yu; Trullinger, Tony K.; Hunter, Ricky; Buysse, Ann M.; Kubota, Asako; LePlae, Jr., Paul Renee; Knueppel, Daniel; Lowe, Christian T.; Pernich, Dan; Demeter, David A.; Johnson, Timothy C.; US2013/109566; (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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H6N2O2

To a solution of i-methyl-I H-pyrazole-5-carboxylic acid (5.28 g, 41.9 mmol) in dichloromethane (55 ml) was added oxalyl chloride (9.14 ml, 104.8 mmol) followed by 3 drops of dimethylformamide. The reaction was stirred at room temperature for 18 hours before concentration in vacuo. The residue was dissolved in acetonitrile (42 ml) and added dropwise to a cooled solution of 3- (2-chloro-5-methoxyphenyl)pyridine-2,6-diamine (preparation 1 , 9.5 g, 38 mmol) and lutidine (6.6 ml, 57.1 mmol) in acetonitrile (650 ml). The reaction was allowed to warm to room temperature and stirred under nitrogen for 2 hours. The reaction was quenched by the addition of water (300 ml) and concentrated to low volume in vacuo. The aqueous residue was washed with dichloromethane (2×300 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with ethylacetate: heptane 1 :4 to furnish a solid. This was recrystallised from toluene (100 ml) to afford 6.7 g of the title product. LCMS Rt=1.88 min MS m/z 358 [MH]+1HNMR (alphafe-DMSO): 3.75 (s, 3H), 4.05 (s, 3H), 5.3 (br s, 2H), 6.9 (m, 1 H), 6.95 (m, 1 H), 7.2 (m, 1 H), 7.3 (m, 1 H), 7.35 (m, 1 H), 7.45 (m, 1 H), 7.5 (m, 1 H), 10.3 (br s, 1 H).

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; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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 II-H18 (150 mg, 0.39 mmol) in acetone (3 mL) were added lH-pyrazole-4- carbonitrilev (43.6 mg, 0.47 mmol) and K2CO3(l08 mg, 0.78 mmol). After stirring at 25C for 14 h, the mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 30 mL). The organic solution was separated, dried over Na2S04, filtered and concentrated. The residue was purified by flash column (20-50% of EtOAc in PE) to give II-H19 (76 mg) as a solid. The solid was further purified by HPLC separation (column: Xtimate C18 (2903) l50*25mm*5um, gradient: 67-87% B (water(0.225%FA)-ACN), flow rate: 25 mL/min) to give II-H19 (43 mg) as a solid. (2904) 1H NMR (400 MHz, CDC13) dH 7.86 (s, 1 H), 7.81 (s, 1 H), 5.05-4.84 (m, 2 H), 2.66-2.57 (m, 1 H), 2.30-2.13 (m, 1 H), 2.10-2.05 (m, 1 H), 1.90-1.95 (m, 7H), 1.53-1.40 (m, 3H), 1.36- 1.22 (m, 8 H), 1.14 – 0.80 (m, 4 H), 0.82 – 0.72 (m, 1 H), 0.68 (s, 3 H); LC-ELSDE/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

These common heterocyclic compound, 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, 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

A solution of compound from step a (775 mg, 5 mmol), 1-chloro-2-(2-chloroethoxy)ethane (1420 mg, 10 mmol), KI (1660 mg, 10 mmol) and K2CO3 (2070 mg,15 mmol) in DMF (60 mL) was stirred for 3 hours at 120 oC. The solvent was removed and it was purified by reverse phase C18 column chromatography (MeCN/H2O) to give desired compound as a light yellow solid. (450 mg, 40%). ESI-MS m/z: 226.0 [M+H]+.

The synthetic route of Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; SHOOK, Brian, C.; KIM, In, Jong; BLAISDELL, Thomas, P.; YU, Jianming; PANARESE, Joseph; LIN, Kai; RHODIN, Michael, H.J.; McALLISTER, Nicole, V.; OR, Yat, Sun; (447 pag.)WO2019/67864; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10199-68-5, name is 4-Phenyl-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 10199-68-5, HPLC of Formula: C9H8N2

[0464] a mixture consisting of compound 21a (500 mg, 2.12 mmol), compound 21b (306 mg, 2.12 mmol) and Cs2CO3 (2.07 g, 6.36 mmol) was stirred at 110.6 C for 16 hrs. The reaction mixture was cooled to room- temperature, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography (petroleum ether: ethyl acetate = 3:2 and then acetic acid: ethyl acetate = 1: 100) to afford compound 21c (80 mg, 12.61% yield) as a light yellow solid, and compound 21d (125 mg, 21.73% yield) as a yellow solid.

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

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, 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. HPLC of Formula: C10H9IN2

General procedure: To iodopyrazole (1 mmol) dissolved in THF (10 mL), Fuajasite (250 mg) was added. Nitric acid (d 1.52 g/cm3, 10 mL) was added slowly and the mixture was stirred at room temperature for required time. The catalyst was recovered by filtration and the filtrate was extracted repeatedly with dichloromethane. The solvent was removed under vacuum to obtain nitropyrazole.

The synthetic route of 1-Benzyl-4-iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ravi; Tewari, Surya P.; Catalysis Communications; vol. 42; (2013); p. 35 – 39;,
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 96799-02-9 as follows. Quality Control of 5-(Furan-2-yl)-1H-pyrazol-3-amine

EXAMPLE 50 6-Fluoro-3-[(5-furan-2-yl-1H-pyrazol-3-ylamino)-methylene]-1,3-dihydro-indol-2-one The named compound is prepared by substituting E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one for E & Z-3-[(hydroxy)-methylene]-1,3-dihydro-indol-2-one and 5-furan-2-yl-1H-pyrazol-3-ylamine for 3-aminopyrazole in the reaction of Example 1. Specifically, E & Z-3-[(hydroxy)-methylene]-6-fluoro-1,3-dihydro-indol-2-one (0.033 gms.) is reacted with 0.061 gms. 5-furan-2-yl-1H-pyrazol-3-ylamine by refluxing in tetrahydrofuran (0.88 mL) to afford the named compound in the amount of 0.0263 gms.

According to the analysis of related databases, 96799-02-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US6559173; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics