Day: September 18, 2021

Synthetic Route of 2075-46-9,Some common heterocyclic compound, 2075-46-9, name is 4-Nitro-1H-pyrazole, molecular formula is C3H3N3O2, 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.

Step2:[00394] To a stirred mixture of iron (1.68g, 30 mmol), ammonium chloride (540mg, 10 mmol), water (2ml_) and ethanol (8ml_) at 800C was added 4-nitro-1 H-pyrazol (1 .13g, lOmmol) in portions. After completion of addition, the mixture was stirred at 800C for additional 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, and the resultant mixture was filtered through a pad of celite. The filtrate was concentrated to afford the crude title compound which was used at next step without further purification. MS (ES) [M+H]+ expected 84.0, found 84.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2008/8375; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 55864-87-4, These common heterocyclic compound, 55864-87-4, name is Ethyl 4-nitro-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.

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (6.40 g, 34.6 mmol) and 10% Pd/C (650 mg) in EtOH (150ml) was stirred under an atmosphere of hydrogen for 20 h. The mixture was filtered through a plug of Celite, reduced in vacuo and dried through azeotrope with toluene to afford 4-amino-1H-pyrazole-3- carboxylic acid ethyl ester as a pink solid (5.28 g, 98%). (1H NMR (400 MHz1 DMSO-d6) D 12.7 (s, 1 H), 7.1 (s, 1 H), 4.8 (s, 2H), 4.3 (q, 2H), 1.3 (t, 3H)).

The synthetic route of 55864-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77424; (2006); A1;; ; Patent; ASTEX THERAPEUTICS LIMITED; WO2006/77425; (2006); 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. 118430-73-2, name is 3-(tert-Butyl)-1-methyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., SDS of cas: 118430-73-2

5-Amino-3-tert-butyl-1-methylpyrazole (1.32 g) was added to a stirred solution of phenyl {3- [ (2-chloropyrimidin-5-yl) ethynyl] phenyl} carbamate (Intermediate 35) (2.0 g) in THF (120 mL) and triethylamine (1.2 mL) and the reaction mixture was heated at 65C for 8 hours. The solvent was evaporated and the residue was triturated with ether/DCM to give the title compound as an off-white solid (1.5 g, 64%); MS m/e MHF 409.

The synthetic route of 118430-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/60970; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3469-69-0,Some common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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.

Step 1 In a flask were combined 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), cyclopropylboronic acid (886 mg, 10.3 mmol) and sodium carbonate (1.09 g, 10.3 mmol) and the mixture suspended in 1,2-dichloroethane (20 mL). A suspension of copper (II) acetate (936 mg, 5.16 mmol) and 2,2-bipyridine (805 mg, 5.16 mmol) in 1,2-dichloroethane (40 mL) was warmed to 50 C. and added and the resulting mixture heated at 70 C. overnight. The mixture was then cooled and filtered and the solids rinsed with EtOAc. The combined filtrates were concentrated and the residue taken up in EtOAc and 50% saturated aqueous NH4Cl. The organic layer was washed with sat NH4Cl, sat NaHCO3 and sat NaCl and dried over MgSO4. The solution was concentrated and the residue purified by SiO2 chromatography (5-35% EtOAc/heptane) to afford 517 mg (43%) 1-cyclopropyl-4-iodo-1H-pyrazole as a colorless oil.

The synthetic route of 3469-69-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hendricks, Robert Than; Hermann, Johannes; Kondru, Rama; Lou, Yan; Lynch, Stephen M.; Owens, Timothy D.; Soth, Michael; US2011/230462; (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. 15802-80-9, name is 3-(tert-Butyl)pyrazole, A new synthetic method of this compound is introduced below., Product Details of 15802-80-9

Sodium hydride (60% suspension in oil, 0.12 g, 3.0 mmol) was washed with hexane, dried under nitrogen and resuspended in dry dimethylformamide (10 mL). 3-tert-butylpyrazole (0.20 g, 1.6 mmol) was added in one portion at ambient temperature, and the stirring was continued until the gas evolution subsided. The (5,11-dihydro-pyrido [2,3-b] [1,5] benzodiazepin-6-yl)- [4-fluoro-2-trifluoromethylphenyl]-methanone of Example 4, Step B (0.50 g, 1.3 mmol) was added in one portion to the clear solution. The mixture was placed in an oil bath (preheated at 130C) for 30 minutes and then heated at reflux for 5 hours. After cooling, the mixture was partitioned between water and ethyl acetate. The organic extracts were dried over sodium sulfate and evaporated to dryness. The crude residue was dissolved in dichloromethane and absorbed onto a silica Merck-60 flash column. Elution with 25% ethyl acetate in hexane provided the title product (0.23 g, 36.0%) as a foam which crystallized by trituration with hexane-ether, m.p. 136-140C. NMR (DMSO-d6, 400 MHz): delta 1.26 (s, 9H, C(CH3)3), 4.17 and 5.45 (dd, 2H, CONCH2), 6.47 (m, 1H, pyrazole CH), 6.54 (m, 1H), 6.68 (m, 1H), 6.80 (m, 1H), 7.00 (m, 1H), 7.28 (m, 1H), 7.60 (m, 1H), 7.87 (m, 1H), 8.04 (m, 1H), 8.13 (m, 1H), 8.47 (m, 1H, pyrazole CH), 9.62 (s, 1H, NH) MS (EI, m/z): 491 [M]+ Anal. Calc’d for C27H24F3N5O: C 65.98, H 4.92, N 14.25. Found: C 65.75, H 4.92, N 13.95

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; Wyeth; EP1000059; (2004); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 4-fluorobenzonitrile (2.49 g, 20.6 mmol) and 4-formylpyrazole (1.98 g, 20.6 mmo) in 50 mL of DMF at 0 0C was added 95percent sodium hydride (0.54 g, 22.7 mmol) under nitrogen. The mixture was heated to 60 0C for 6 hours and cooled to room temperature, Water was added carefully and the mixture was then extracted with ethyl acetate. The combined extracts were washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 4~(4-formyMH-pyrazol-l-yl)benzonitrile.

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-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; DI MARCO, Christina, Ng; WO2010/19391; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 131797-35-8, name is 5-Chloro-3-(trifluoromethyl)-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 131797-35-8, Product Details of 131797-35-8

To a solution of 2-chloro-7-(chloromethyl)-N-ethyl-5-oxo-5H-[l,3]thiazolo[3,2-a]pyrimidine- 3-carboxamide (2 g, 6.53 mmol) in acetonitrile (10 mL) was added 5-chloro-3-(trifluoromethyl)-lH- pyrazole (872 mg, 5.11 mmol), potassium iodide (542 mg, 3.26 mmol), and potassium carbonate (1.8 g, 13 mmol). The resulting mixture was stirred for 1 h at 80 C and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/petroleum ether (1/1) to afford of 2-chloro-7-[[5-chloro-3-(trifluoromethyl)-lH-pyrazol-l-yl]methyl]-N-ethyl-5-oxo-5H- [l,3]thiazolo[3,2-a]pyrimidine-3-carboxamide (1.1 g, 38%) as a yellow solid. LCMS (ESI): M+H + = 441.0.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; YU, Jiang; WU, Guosheng; YUEN, Po-Wai; VILLEMURE, Elisia; SCHWARZ, Jacob; LY, Cuong; SELLERS, Benjamin; VOLGRAF, Matthew; WO2015/52226; (2015); 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. 96799-02-9, name is 5-(Furan-2-yl)-1H-pyrazol-3-amine, A new synthetic method of this compound is introduced below., Computed Properties of C7H7N3O

A solution of 3-amino-5-(2-furyl)pyrazole (162 mg, 1.09 mmol) and DIPEA (0.19 mL, 1.09 mmol) in THF (5 mL) was added dropwise to a solution of cyanuric chloride (200 mg, 1.09 mmol) in THF (16.0 mL) at 0 0C. The reaction mixture was stirred at 0 C to room temperature for 2 hours. Then, 1-metyl piperazine (0.12 mL, 1.09 mmol) and DlPEA (0.19 mL, 1.30 mmol) were added to the mixture. The mixture was allowed to stir at room temperature for 3 hours. The solids were filtered off to give compound 11 as white solid (1 10 mg, 14 %). %). 1H NMR (400 MHz, DMSOd6) delta 12.92 (s, IH, NH), 10.38 (s, IH, NH), 7.76 (s, IH, Ar-H), 6.816.61 (m, 3H, Ar-H), 3.77-3.72 (m, 4H, 2CH2), 2.38-2.35 (m, 4H, 2CH2), 2.21 (2, 3H, CH3); ESI-MS: calculated for (C15Hi7ClN8O) 360, found 361 [M+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; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; HO, David; DESAI, Neil, P.; WO2010/144550; (2010); A1;,
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 1227611-94-0 as follows. Formula: C9H11IN2O

Intermediate 28: 4-Iodo-1 -(1 -oxa-spiro[2.5]oct-6-yI)-1 H -pyrazole 2-Methyl-propan-2-ol potassium (466 mg; 4.15 mmol; 1.2 eq.) was added in one portion to a solution of 4-(4-Iodo-pyrazol-1-yI)-cyclohexanone (1.02 g; 3.50 mmol; 1.0 eq.) and trimethylsulfoxonium chloride (531 mg; 4.13 mmol; 1.2 eq.) in DMSO (50 mL). The reaction mixture was stirred at RT for 16 h. It was then poured into EtOAc . Organicphase was separated and washed with brine (three times), dried over magnesium sulfate, filtered and concentrated to give the title compound a white solid (813 mg, 76%).1H NMR (300 MHz, DMSO) oe8.01 (d, J = 0.5 Hz, 1H), 7.52 (d, J = 0.5 Hz, 1H), 4.41 -4.26(m, 1H), 2.66 (s, 2H), 2.13- 1.85 (m, 6H), 1.34- 1.21 (m, 2H). MS(ESI+): 305.1.

According to the analysis of related databases, 1227611-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARES TRADING S.A.; CROSIGNANI, Stefano; JORAND-LEBRUN, Catherine; GERBER, Patrick; MUZERELLE, Mathilde; WO2014/8992; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature 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.

21F. 2-((4-(5-Cyclopropyl-lH-pyrazol-3-ylamino)pyrrolo [1,2-f][l,2,4]triazin-2- yl)methyl)isoindoline-l,3-dione. 2-((4-Chloropyrrolo[l,2-/|[l,2,4]triazin-2-yl)methyl)isoindoline-l,3-dione (4.43 g, 14.17 mmol) was suspended in NMP (50 mL), then DIPEA (4.95 mL, 28.3 mmol) was added. The mixture was heated to 80 0C, to which was slowly added via syringe a solution of S-cyclopropyl-lH-pyrazol-S-amine (3.49 g, 28.3 mmol) in NMP (20 mL). The reaction was stirred at 80 0C for 2 h, then cooled to room temperature. The reaction was diluted with EtOAc (700 mL) and washed with water (3 x 500 mL) and brine (2 x 250 mL). The organics were dried (MgSO4), filtered, and concentrated in vacuo. The residue was dissolved in a minimum of EtOAc and diluted with hexanes, and the precipitate was filtered and dried. The solids were triturated twice with 20% EtOAc/Hex, once with 20% DCM/Hex, and finally in 50% DCM/Hex to give 21F (3.35 g, 59%). 21F had an analytical HPLC retention time = 3.368 min (Phenomonex-Luna (4.6 x 50 mm SlO); 10-90% MeOH/H2O (0.1% TFA) over 4 min; flow = 4 mL/min) and a LC/MS M+ +1 = 400.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/131050; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics