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 2458-26-6 as follows. Recommanded Product: 2458-26-6

Aromatic substrate 1b (0.1mmol), 3-phenylpyrazole 2m (0.15mmol), cuprous bromide (0.1mmol), potassium acetate (0.2mmol), DMSO (1.0mL) were added to the 15mL Schlenk tube, then directly sealed tube at 85 C for 12h. After the reaction was completed, the mixture was cooled to room temperature, and a small amount of ethyl acetate and ammonia were added to quench the reaction. The ethyl acetate was repeatedly extracted. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered under reduced pressure, and the solvent was evaporated under reduced pressure. The crude product was separated and purified by a preparative plate (DCM: MeOH = 35: 1) to obtain 3bm as a white solid, 29.4 mg, with a yield of 70%.

According to the analysis of related databases, 2458-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Laishi Blood Goods Co., Ltd.; Wang Peng; Yu Jinfeng; Li Jianjun; (32 pag.)CN110386929; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-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 2075-46-9, Safety of 4-Nitro-1H-pyrazole

Step 1: Preparation of 3-chloro-1H-pyrazol-4-amine hydrochloride Into a 2 L three-necked round bottom flask affixed with an overhead stirrer, a temperature probe, an addition funnel, and a nitrogen inlet were added ethanol (600 mL) and 4-nitro-1H-pyrazole (50.6 g, 447 mmol). To this solution was added, in one portion, conc. HCl (368 mL) (note: rapid exotherm from 15 C. to 39 C.) and the resulting mixture was purged with nitrogen for 5 minutes. Palladium on alumina (5% w/w) (2.6 g, Alfa, black solid) was added to the mixture and stirred at room temperature while triethylsilane (208 g, 1789 mmol) was added drop-wise over 4 h. The reaction, which started to slowly exotherm from 35 C. to 55 C. over 2.0 h, was stirred for a total of 16 h and vacuum filtered through a plug of Celite to give a biphasic mixture. The mixture was transferred to a separatory funnel, the bottom aqueous layer was collected and rotary evaporated (60 C., 50 mmHg) to dryness with the aid of acetonitrile (3*350 mL). The resulting yellow solid was suspended in acetonitrile (150 mL) and allowed to stand for 2 h at room temperature followed by 1 h at 0 C. in the refrigerator. The solids were filtered and washed with acetonitrile (100 mL) to afford the titled compound 3-chloro-1H-pyrazol-4-amine hydrochloride (84 g, 97% yield, 80% purity) as a white solid: mp 190-193 C.; 1H NMR (400 MHz, DMSO-d6) delta 10.46-10.24 (bs, 2H), 8.03 (s, 0.54H), 7.75 (s, 0.46H), 5.95 (bs, 1H)); 13C-NMR (101 MHz, DMSO) delta 128.24, 125.97, 116.71.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; US2013/288893; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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.

Example 10; 3-{[4-(Azetidin-l-ylcarbonyl)phenvnoxy}-iV-(5-methyl-lH-pyrazol-3-yl)- 5- [(3S)-tetr ahydrofur an-3-yloxyl benzamide; l-Chloro-N,N,2-trimethyl-l-propenylamine (0.145 mL, 1.10 mmol) was added to a solution of 3-{ [4-(azetidin- 1 -ylcarbonyl)phenyl]oxy } -5-[(3S)-tetrahydrofuran-3- yloxy]benzoic acid (350 mg, 0.92 mmol) in DCM (6 mL) and stirred at RT for 30 – 40min. 1,1-Dimethylethyl 3-amino-5-methyl-lH-pyrazole-l-carboxylate (361 mg, 1.83 mmol) and pyridine (0.148 mL, 1.83 mmol) were added and the reaction stirred at RT for 2 hours. The solvent was removed in vacuo, water (20 mL) added and the mixture extracted with ethyl acetate (3 x 20 mL). The extracts were combined and washed with 2Nu hydrochloric acid (20 mL), a saturated solution of sodium bicarbonate (20 mL), water (20 mL), brine (20 mL), dried (MgSO4) and evaporated in vacuo. The crude product was chromatographed on silica, eluting with a gradient of 0- 10% methanol in DCM, to give a white solid which was taken up in acetonitrile (2 mL) and heated in a microwave reactor at 160C for 10 minutes. EPO The reaction mixture was evaporated and the residue chromatographed on silica, eluting with 0-5% methanol in DCM, to give the desired compound as a white foam (50 mg). 1H NMR delta (CDCl3): 2.11 – 2.29 (m, 2H), 2.32 (s, 3H), 2.32 – 2.40 (m, 2H), 3.88 – 4.02 (m, 4H), 4.23 (t, 2H), 4.35 (t, 2H), 4.95 – 4.99 (m, IH), 6.56 (s, IH), 6.71 (t, IH), 7.02 (d, 2H), 7.13 (s, IH), 7.21 (s, IH), 7.64 (d, 2H), 9.06 (s, IH); m/z 463 (M+H)+, 461 (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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/17649; (2007); 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

A solution of Intermediate 55a (2.64 g, 6.50 mmol), 3-tert-butyl-1H-pyrazole-5-amine (997 mg, 7.1 mmol) and trans-N,N?-dimethylcyclohexane-diamine (185 mg, 0.33 mmol) was formed in toluene (25 mL). Potassium carbonate (1.9 g, 13.7 mmol) was added and the mixture degassed by bubbling nitrogen through it. Copper(I) iodide (64.0 mg, 1.30 mmol) was added and the mixture was refluxed at 110 C. for 24 h. The solvent was evaporated under reduce pressure and the residue was partitioned between EtOAc/Water and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered and evaporated. Purification by FCC eluting with a gradient of 0-50% EtOAc in cyclohexane gave the title compound (1.72 g, 64%). LCMS (Method 3): Rt 3.69 min, m/z 418 [MH+].

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; CHIESI FARMACEUTICI S.p.A.; Alcaraz, Lilian; Hurley, Christopher; Cridland, Andrew Peter; Jennings, Andrew Stephen Robert; US2014/364412; (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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 5334-40-7

Synthesis of 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester A 20 L reaction vessel equipped with a digital thermometer and stirrer was charged with 4-nitro-1H-pyrazole-3-carboxylic acid (1.117 Kg, 7.11 mol, 1 wt) and methanol (8.950 L, 8 vol). The reaction mixture was stirred under nitrogen, cooled to 0 to 5 C., thionyl chloride (0.581 L, 8.0 mol, 0.52 vol) added over 180 minutes and the resultant mixture allowed to warm to and stir at 18 to 22 C. overnight after which time 1H NMR analysis (d6-DMSO) indicated reaction completion. The reaction mixture was concentrated under reduced pressure at 40 to 45 C., the residue treated with toluene and re-concentrated (3*2.250 L, 3*2 vol) under reduced pressure at 40 to 45 C. to give 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester as an off-white solid (1.210 Kg, 99.5% th).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/55094; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 2075-45-8, The chemical industry reduces the impact on the environment during synthesis 2075-45-8, name is 4-Bromo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

4-bromopyrazole (15.6 g, 0.1 mol), ethyl iodide (10.9 g, 0.1 mol), tetrabutylammonium iodide (3.7 g, 0.01 mol) at room temperature,Dissolved in 5 ml of dimethyl sulfoxide (DMSO), and added with sodium hydroxide solution [sodium hydroxide solution: a solution obtained by dissolving 4.4 g (0.11 mol) of sodium hydroxide in 5 ml of water],The reaction is exothermic. After the addition is completed, it is stirred at room temperature overnight, diluted with water and diluted with dichloromethane.Drying, concentration and distillation under reduced pressure gave 16.8 g of 1-ethyl-4-bromo-1H-pyrazole.The yield was 96.0%.

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (16 pag.)CN108863936; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 10010-93-2, The chemical industry reduces the impact on the environment during synthesis 10010-93-2, name is 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

[0151] To a solution of 5-methyl-3-(trifluoromethyl)-lH-pyrazole (6.0 g, 30 mmol, 1 eq) in CH3CN (60 mL), were added I2 (7.6 g, 30 mmol, 1 eq) and CAN (8.22 g, 15 mmol, 0.5 eq) in one portion. Then the mixture was stirred at room temperature overnight. TLC indicated the reaction was completed. The reaction mixture was poured into ice water and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (3×40 mL), aq.Na2S03 (2×30 mL), dried over Na2S04 and concentrated in vacuum to give crude product, which was purified by column chromatography on silica gel to give4-iodo-5-methyl-3- (trifluoromethyl)-lH-pyrazole (5.0 g, yield: 60.6%); LC/MS: m/z (M++l) = 277.

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, 3-Methyl-5-(trifluoromethyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMARESOURCES (SHANGHAI) CO., LTD.; CHEN, Ping; ZHOU, Ding; SHAO, Shaoping; CAI, Zhen-wei; WO2013/6792; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 79080-31-2, 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. 79080-31-2 name is 1,5-Dimethyl-3-(trifluoromethyl)-1H-pyrazole, 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.

EXAMPLE 9 In a 100 ml of an autoclave made of Hasteroy C-276 were charged 50 ml of acetic acid, 8.2 g (50 mmole) of 1,5-dimethyl-3-trifluoromethylpyrazole, 0.249 g (1 mmole) of cobalt acetate, 0.123 g (0.5 mmole) of manganese acetate and 0.204 g (2 mmole) of sodium bromide, reaction and operation were carried out in the same manner as in Example 1. A conversion ratio of the starting 1,5-dimethyl-3-trifluoromethylpyrazole was 96.8%, and a yield of 1-methyl-3-trifluoromethylpyrazole-5-carboxylic acid was 52.0%.

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

Reference:
Patent; Nissan Chemical Industries, Ltd.; US5053517; (1991); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 175277-11-9,Some common heterocyclic compound, 175277-11-9, name is 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, molecular formula is C9H14N2O2, 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.

46) 3-(tert-butyl)-N-(6-fluoro-2,3-dimethoxybenzyl)-1-methyl-1H-pyrazole-5-carboxamide To a solution of aldehyde (250 mg, 1.36 mmol, 1.0 eq) in toluene (15 mL) was added 2,4-dimethoxybenzyl amine (227 mg, 1.36 mmol, 1.0 eq) and the reaction mixture was stirred at room temperature for 24 h. Toluene was removed to give a residue, which was taken in MeOH (15 mL) and then NaBH4 (103 mg, 2.72 mmol, 2.0 eq) was added slowly. The reaction mixture was stirred at room temperature for 6 h. Solvent was removed and the residue was extracted in Ethyl acetate and stirred with saturated aq NaHCO3 for 1 h. The organic layer was collected, dried and solvent was removed to give the crude amine, which was used in the next step without further purification. To a solution of the crude amine (0.45 mmol, 1.1 eq) in DMF (5 mL) were added the acid (75 mg, 0.407 mmol, 1.0 eq), DIEA (262 mg, 2.04 mmol, 5 eq) and HBTU (205 mg, 0.54 mmol, 1.2 eq) and the reaction mixture was stirred at rt for 12 h. The reaction mixture was then diluted with ethyl acetate (20 mL) and washed with 10% aq HCl (1*20 mL), sat NaHCO3 (1*20 mL) and water (4*20 mL). Organic layer was collected, dried (MgSO4) and evaporated to give a crude product, which was purified by column chromatography (EtOAc/Hexane 25% to 75%)) to give the amide, which was directly used in the next step. The amide was treated with 95% TFA:H2O for 12 h. TFA was removed and azeotroped with toluene to give a residue, which was purified by column chromatography (EtOAc/Hexane 10% to 50%) to give the desired product. Mass Spectrum (LCMS, ESI Pos.) Calcd. For C18H25FN3O3: 350.0 (M+H), Found 350.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-tert-Butyl-1-methylpyrazole-5-carboxylic Acid, its application will become more common.

Reference:
Patent; Prosetta Antiviral ,Inc.; Selvarajah, Suganya; Paulvannan, Kumar; (58 pag.)US2018/118679; (2018); 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. 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., name: 1H-Pyrazole-3-carboxylic acid

Ethyl 1H-pyrazole-3-carboxylate (6) A 100 mL Schlenk tube was dried under vacuum, filled with nitrogen and charged with 0.5 g (4.461 mmol, 1.0 eq) 1H-pyrazol-3-carboxylic acid which was dissolved in 20 mL EtOH. After adding 1.31 g (0.72 mL, 13.382 mmol, 3.0 eq) conc. H2SO4 the colorless reaction mixture was heated to reflux (100° C.) and stirred at this temperature for 4 h. TLC analysis (DCM/MeOH 95:5) indicated full conversion of the starting material. After cooling to rt the mixture was transferred to a flask to remove the solvent at a rotary evaporator. The colorless residue was diluted in 20 mL water and neutralized with 17 mL saturated aqueous NaHCO3 solution. Thereby a white solid precipitated. The aqueous layer was extracted with EtOAc (4*50 mL), dried over MgSO4 and the solvent was evaporated under reduced pressure to yield the pure title compound. yield: 582.5 mg (93percent); colorless solid; M.p.: 158-161° C.; Rf (DCM/MeOH 95:5): 0.42; 1H-NMR (300 MHz, CDCl3): delta (ppm)=10.69 (bs, 1H, NH), 7.84 (d, 4J=2.1 Hz, 1H, Ar-H), 6.86 (d, 4J=2.1 Hz, 1H, Ar-H), 4.43 (q, 3J=7.2 Hz, 2H, CH2), 1.41 (t, 3J=7.2 Hz, 3H, CH3); 13C-NMR (75.5 MHz, CDCl3): delta (ppm)=161.8 (C=O), 141.6 (Cq), 132.3 (CHAr), 107.8 (CHAr), 61.1 (CH2), 14.3 (CH3); GC-MS (NM-50_S2): tR=4.655 min (m/z=140.1, 98.0percent M+, BP: 95.0).

The synthetic route of 1621-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Technische Universitaet Graz; Karl-Franzens-Universitaet Graz; Schweiger, Martina; Romauch, Matthias; Zimmermann, Robert; Mayer, Nicole; Breinbauer, Rolf; US9206115; (2015); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics