Category: pyrazoles-derivatives

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. 13808-64-5, name is 4-Bromo-3-methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C4H5BrN2

Step A: N-Boc-4-bromo-3-methyl-pyrazole. To 4-bromo-3-methyl-pyrazole (3.50 g, 21.7 mmol) was added CH2Cl2 (30 mL), di-tert-butyl dicarbonate (5.22 g, 23.9 mmol) and aq Na2CO3 (1 M, 43.5 mL). The reaction was stirred for 2.5 h and the aq portion was then separated. The CH2Cl2 portion was then washed with 5% citric acid followed by brine/saturated aq NaHCO3 (1:1). The solution was dried (Na2SO4), filtered and concentrated to afford the product.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Clements, Matthew J.; Debenham, John S.; Hale, Jeffrey J.; Madsen-Duggan, Christina B.; Walsh, Thomas F.; Peresypkin, Andrey V.; Helmy, Roy; US2008/269279; (2008); 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. 2075-45-8, name is 4-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 2075-45-8

Preparation 45 4-Bromo-1-trityl-1H-pyrazole Trityl chloride (9.02 g) was added to a stirred solution of 4-bromopyrazole (4.24 g) and 4-dimethylaminopyridine (0.711 g) in pyridine (90 ml). The reaction mixture was heated to 85 C. for 20 hrs, cooled to room temperature and partitioned between diethyl ether and water. The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. The crude product was recrystallized from hexane/toluene (5/1, 180 ml) to afford the title compound (4.0 g). The remaining solids and the mother liquors were combined and purified by column chromatography on silica gel eluding with pentane/ether (30/1, v/v) to afford a second batch of title compound (3.0 g). deltaH (300 MHz, CDCl3): 7.60 (1H, s), 7.40 (1H, s), 7.30 (9H, m), 7.20 (6H, 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; Pfizer Inc.; US6200978; (2001); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35277-02-2,Some common heterocyclic compound, 35277-02-2, name is 4-Fluoro-1H-pyrazole, molecular formula is C3H3FN2, 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 5-chloropyrazine-2-carbonitrile (280 mg, 2.0 mmol) in DMF was added 4-fluoro-1H-pyrazole (170 mg, 2.0 mmol), and potassium acetate (395 mg, 4.0 mmol). The mixture was stirred at the 100C for 4 hours. The reaction mixture was cooled to 20C, poured into brine (25 mL), and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and purified by column chromatography (hexane: ethyl acetate = 5:1) to give 5-(4-fluoro-1H-pyrazol-1- yl)pyrazine-2-carbonitrile (310 mg, Yield 82%). The structure was confirmed by LC-MS.

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

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; BRUBAKER, Jason D.; GUZI, Timothy; WILSON, Kevin J.; DIPIETRO, Lucian V.; ZHANG, Yulian; WILSON, Douglas; FLEMING, Paul E.; (137 pag.)WO2018/17983; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3112-31-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3112-31-0 name is 1H-Pyrazole-3,5-dicarboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of pyrazole-3,5-dicarboxylic acid (75 g, 431 mmol) in 11 of anhydrous methanol was treated with anhydrous HCl gas. The HCl addition was continued for 30 min after which, the solution was allowed to cool to room temperature and allowed to stand for 16 h. The solution was then heated at reflux for 3 h then cooled and the solvent removed at reduced pressure. The resulting white solid was treated with 600 ml of saturated NaHCO3 and extracted into CH2 Cl2 (3*500 ml). The pooled extracts were dried (Na2 SO4), filtered and evaporated at reduced pressure. The resulting white solid was recrystallized from methanol with the addition of anhydrous ether to give dimethyl pyrazole-3,5-dicarboxylate (3-1a). 1 H NMR (CDCl3) delta 7.38 (s, 1H); 3.98 (s, 3H); 3.93 (s, 3H).

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

Reference:
Patent; Merck & Co., Inc.; US5821241; (1998); A;,
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. 84547-86-4, name is 4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-1-methyl-1H-pyrazole-3-carboxylic acid

A mixture of methyl 4-bromo-1-methyl-1H-pyrazole-3-carboxylic acid (1eq), 4,4,4′,4′,5,5,5′,5′- octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1 eq), KOAc (2 eq) and Pd(dppf)Cl2 (5 mol%) in 1,4- dioxane (10 mL) was stirred at 100 oC overnight. The precipitate was removed by filtration and the filtrate was used for next step without further purification. ESI-MS (m/z): 267.20 [M+1]+.

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 84547-86-4.

Reference:
Patent; ASTRAZENECA AB; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore, M.; HOLENZ, Joerg; WESOLOWSKI, Steven; HE, Yuanjun; BUeRLI, Roland; (201 pag.)WO2017/139603; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1280210-79-8, These common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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.

To a suspension of sodium hydride (60% dispersion in oil, 1.55 g, 38.7mmol) in anhydrous acetonitrile (200 mL) was added to tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole- 5(4H)-carboxylate (5.3 g, 25.5 mmol) in one portion under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 2 h. To the resulting white suspension was slowly added cyclopropanesulfonyl chloride (6.9 g, 49.1 mmol) and the mixture was stirred at room temperature for 18 h, quenched with water (120 mL) and the layers were separated. The aqueous layer was then extracted with dichloromethane (2 x 100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material was purified on silica chromatography (300 g Biotage column) and eluted with 15-80% ethyl acetate in hexanes to yield the title compound and tert-butyl 1 -(cyclopentylsulfonyl)-2,6-dihydro^ as a white solid.LC/MS: 314.2(M+1).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HICKS, Jacqueline, D.; BIFTU, Tesfaye; CHEN, Ping; QIAN, Xiaoxia; WILKENING, Robert, R.; WO2011/146358; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products 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 tert-butyl {4-methyl-2-[2-(trifluoromethyl)benzyl]-1,3-thiazol-5-yl}carbamate (400 mg, 1.07 mmol) obtained in Example 209-D) in ethanol (10 mL) was added dropwise concentrated hydrochloric acid (4.8 mL) at room temperature, and the mixture was stirred at 50C for 1.5 hr. The reaction mixture was cooled to room temperature, neutralized with 8M aqueous sodium hydroxide solution, adjusted to pH 10-11 with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in DMA (10 mL), and 1-methyl-1H-pyrazole-5-carboxylic acid (161 mg, 1.28 mmol), HATU (487 mg, 1.28 mmol) and DIEA (0.0884 mL, 0.535 mmol) were added at room temperature. The reaction mixture was stirred at 80C overnight. After cooling to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: hexane-ethyl acetate (13:7-7:13)] and basic silica gel column chromatography [eluent: hexane-ethyl acetate (7:3-1:1)], and crystallized from ethyl acetate-hexane to give the title compound (107 mg) as white crystals (yield 26%). MS (ESI+): [M+H]+ 381. 1H NMR (300 MHz, DMSO-d6) delta 2.30 (3H, s), 4.03 (3H, s), 4.39 (2H, s), 7.05 (1H, d, J = 2.3 Hz), 7.51-7.62 (3H, m), 7.69 (1H, d, J = 7.5 Hz), 7.71-7.83 (1H, m), 10.50 (1H, s).

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; Takeda Pharmaceutical Company Limited; EP2530078; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 5334-40-7, These common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, 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.

Step 1: Synthesis of 4-[(4-nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 4-Nitropyrazole-3-carboxylic acid (20.0 g, 127.4 mmol) was suspended in CH2Cl2/DMF (99:1, 400 mL), treated cautiously with oxalyl chloride (11.6 mL, 134 mmol) and then stirred at room temperature for 16 h. The reaction mixture was evaporated then re-evaporated with toluene (*3) to give a yellow solid. The resultant acid chloride was suspended in dioxane (400 mL), treated with triethylamine (26.4 mL, 190 mmol) followed by 4-amino-1-BOC-piperidine (25.0 g, 125 mmol) and stirred at room temperature for 6 h. The reaction mixture was filtered and the solid collected stirred in water (500 mL) and then re-filtered. The solid collected was dried in vacuo, azeotroping with toluene, to give the title compound (37.6 g).

The synthetic route of 5334-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/21420; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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. name: tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate

General procedure: Cbz-Arg(N,N-diBoc)-Val-Sta-NH(CH2)2Ph (69). A mixture of Cbz-Orn(N-Boc)-Val-Sta-NH(CH2)2Ph (52) (65 mg, 0.090 mmol) and 4M HCl in dioxane was allowed to stir for 1 h at 20C. The reaction mixture was concentrated to dryness in vacuo to obtain the crude residue as a on oil. The oil was dissolved in DCM (1 mL) and Et3N (6 muL, 0.043 mmol) was added. The solution was stirred vigorously for 5min. N,N?-bis-Boc-1-guanylpyrazole (13 mg, 0.042 mmol) was added and the solution was allowed to stir for 18 h at 20C. The reaction mixture was concentrated to dryness in vacuo to obtain a crude residue. The crude residue was subjected to a silica chromatography gradient eluting from 100% DCM to 10% MeOH/DCM to obtain Cbz-Arg(N,N-diBoc)-Val-Sta-NH(CH2)2Ph (69) as a solid (46 mg, 53%).

The synthetic route of tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen, William; Hodder, Anthony N.; de Lezongard, Richard Bestel; Czabotar, Peter E.; Jarman, Kate E.; O’Neill, Matthew T.; Thompson, Jennifer K.; Jousset Sabroux, Helene; Cowman, Alan F.; Boddey, Justin A.; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 182 – 198;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57012-20-1, name is (1,3-Dimethyl-1H-pyrazol-5-yl)methanol, 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 57012-20-1, Quality Control of (1,3-Dimethyl-1H-pyrazol-5-yl)methanol

To a stirring solution of (2,5-dimethyl-2H-pyrazol-3-yl)-methanol (100 mg, 0.79 mmol) in diethyl ether (3 ml.) is added PBr3 (25 //L, 0.26 mmol). The reaction is stirred at room temperature for 18 hours, then water is added. The diethyl ether layer is separated and stored over solid NaOH and used in Step 71b without further characterization.

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, (1,3-Dimethyl-1H-pyrazol-5-yl)methanol, other downstream synthetic routes, hurry up and to see.

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