Tag: M.W:100-200

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

PREPARATION EXAMPLES Preparation of compound No. 3 At room temperature, 70 mul (0.8 mmol) of oxal chloride and 30 mul of dimethylformamide are added to a suspension consisting of 130.0 mg (0.7 mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid in 5 ml of dichloromethane. After 2 hours, this reaction mixture is added dropwise to a solution consisting of 160.0 mg (0.7 mmol) of N-cyclopropyl-2-(1,3-dimethylbutyl)aniline and 130 mul (1.0 mmol) of triethylamine in 5 ml of dichloromethane. After 48 hours of stirring at room temperature, 4 ml of water are added and the organic phase is separated off, dried over magnesium sulphate and concentrated under reduced pressure. This gives, after column chromatography (gradient cyclohexane/ethyl acetate), 202.0 mg (0.5 mmol, 72% of theory) of N-cyclopropyl-3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazol-4-carboxamide [log P (pH 2.3) 3.89].

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer CropScience AG; US2009/176844; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 89717-64-6, name is 4-Bromo-3-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 89717-64-6, COA of Formula: C3H2BrN3O2

To a solution of 4-bromo-3- nitro-lH-pyrazole (1.3 g, 6.8 mmol) in DMF (15 mL) was added benzyl bromide (1.72 g, 10.1 mmol) and K2CO3 (1.86 g, 13.5 mmol) at room temperature. The reaction mixture was stirred at 80 C for 12 h. After cooling down to room temperature, the mixture was diluted with water (40 mL) and extracted with EtOAc (40 mL x 2). The combined organic layers were washed with water (30 mL) and brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (eluted with petroleum ether/EtOAc from 0% to 20%) to give the l-benzyl-4-bromo-3-nitro-lH-pyrazole (1.5 g, Yield: 78%) as a yellow solid. ESI-LCMS (m/z): 282.0 [M+1]; 1HNMR (400 MHz, CD3OD): delta 8.05 (s, 1H), 7.43-7.32 (m, 5H), 5.41 (s, 2H) ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; (178 pag.)WO2016/44666; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 71229-85-1, name is 4-Bromo-1-ethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 71229-85-1

Step 4: Synthesis of 6-chloro-2-cyclopropyl-1-(1-ethyl-1H-pyrazol-4-yl)-7-fluoro-1H-indole1003421 To a solution of compound 3 (4.3 g, 20.5 mmol) in toluene (50 mL) were added 4-bromo-1-ethyl-1H-pyrazole 4(4.0 g, 22.8 mmol), potassium phosphate (11.0 g, 51.2 mmol), N,N?dimethylethylenediamine (722 mg, 8.2 mmol) and Cu(I)I (390 mg, 2.0 mmol) at RT under inert atmosphere. The reaction solution was purged with argon for 15 mm and then sealed the tube. The reaction mixture was heated to 140 C and stirred for 16 h. After completion of the reaction by TLC, the reaction mixture was cooed to RT, diluted with EtOAc (50 mL) and filtered. The filtrate was washed with water (40 mL), brine (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified (silica gel chromatography; 9% EtOAc/Hexanes) to afford compound 5 (3.9 g, 63%) as a pale brown solid. 1H NMR (400 MHz, CDC13): oe 7.64 (s, 1H), 7.60 (s, 1H), 7.16 (d, J = 8.4 Hz, 1H), 7.01 (dd, J =8.4, 6.4 Hz, 1H), 6.12 (s, 1H), 4.25 (q, J = 7.2 Hz, 2H), 1.69-1.62 (m, 1H), 1.56 (t, J = 7.2 Hz, 3H), 0.92-0.87 (m, 2H), 0.76-0.72 (m, 2H); LC-MS (ES): 98.6%; mlz 304.3 (M + Hj; (column: X Select C-18, 50 x 3.0 mm, 3.5 jim); RT 4.23 mm; 5 mM NH4OAc: ACN; 0.8 mL/min).

The synthetic route of 71229-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Edward; LONERGAN, David; WO2015/77503; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-40-7, 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. 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Into a 100 mL round bottom flask containing a solution of methyl 4-nitro-1H-pyrazole- 3-carboxylate (5.0 g, 29 mmol) in dimethylformamide (50 mL) were added anhydrous potassium carbonate (8.0 g, 58 mmol) and 2-iodopropane (5.8 mL, 58 mmol) at 0 oC and the mixture was stirred at room temperature for 16 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified flash chromatography eluting with ethyl acetate in petroleum ether (10-20percent) to afford a mixture of regioisomers, methyl 1-isopropyl-4-nitro-1H-pyrazole-5-carboxylate (2.2 g, 35percent yield) as a colorless oil and methyl 1-isopropyl-4-nitro-1H-pyrazole-3-carboxylate as an oil. For methyl 1- isopropyl-4-nitro-1H-pyrazole-5-carboxylate; 1H NMR (CD3OD, 400 MHz): delta 8.16 (s, 1H), 4.75-4.71 (m, 1H), 4.04 (s, 3H), 1.52 (d, J = 6.6 Hz, 6H). For methyl 1-isopropyl-4-nitro-1H- pyrazole-3-carboxylate; 1H NMR (CD3OD, 400 MHz): delta 8.68 (s, 1H), 4.66-4.59 (m, 1H), 3.95 (s, 3H), 1.55 (d, J = 6.7 Hz, 6H).

The chemical industry reduces the impact on the environment during synthesis 4-Nitro-1H-pyrazole-3-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIM, Jongwon; ALTMAN, Michael, D.; BRUBAKER, Jason, D.; GIBEAU, Craig, R.; (94 pag.)WO2016/144847; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

A common compound: 5744-56-9, name is 1,3-Dimethyl-1H-pyrazole-5-carboxylic acid, belongs to pyrazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 5744-56-9

Scheme I 1,3-Dimethyl-4-nitro-pyrazole-5-carboxylic acid One-hundred twelve g concentrated sulfuric acid is added to 42 ml 90% nitric acid at 70-80 C., 39 g of 1,3-dimethylpyrazole-5-carboxylic acid is added in portions over one hour such that the temperature does not go over 90 C. After 2.5 hours the reaction mixture is cooled and poured over ice. The resulting percipitate was filtered, dried, and recrystallized in ethanol, mp 141-142 C.

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, 5744-56-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Warner-Lambert Company; US4666908; (1987); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 138786-86-4, The chemical industry reduces the impact on the environment during synthesis 138786-86-4, name is Methyl 4-nitro-1H-pyrazole-3-carboxylate, I believe this compound will play a more active role in future production and life.

Example 12 Benzyl-(2S)-4-(5-{[(4-amino-1-phenyl-1H-pyrazol-3-yl)amino]carbonyl}pyridin-2-yl)-2-methylpiperazine-1-carboxylate A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1 L of methylene chloride and filtered through a large plug of silica (washing with 2 L methylene chloride). The solvent was evaporated in vacuo to give methyl 4-nitro-1-phenyl-1H-pyrazole-3-carboxylate confirmed by 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

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, Methyl 4-nitro-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hamblett, Christopher; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Wilson, Kevin; US2009/105264; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 15754-60-6, name is 1-(tert-Butyl)-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. Product Details of 15754-60-6

Flash vacuum pyrolysis reactions were carried out by distillation of the substrate in vacuo through an electrically heated silica furnace tube (35 × 2.5 cm). Products were trapped in a U-tube situated at the exit point of the furnace and cooled with liquid N2. Conditions were first established on a small scale (20 mg) where the product(s) were dissolved in a deuterated solvent and analyzed directly by 1H NMR spectroscopy. Larger-scale pyrolyses, involving 0.1 g or more of substrate, were usually removed from the trap by solution in CH2Cl2 (30mL). The precursors and pyrolysis conditions [quantity of precursor, inlet temperature (Ti), furnace temperature (Tf), pressure range (P), and pyrolysis time (t)] and yields are stated. This compound was too volatile for normal inlet conditions. It was therefore cooled in an acetone-dry ice bath, which was slowly removed to allow sublimation (20 mg, Ti acetone/dry ice bath, Tf 600-850 C, P 0.03 Torr, t 15 min).

The synthetic route of 1-(tert-Butyl)-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mackay, Martha; Nortcliffe, Andrew; McNab, Hamish; Hulme, Alison N.; Synthesis; vol. 47; 2; (2015); p. 242 – 248;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 4054-67-5, name is 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole, 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. SDS of cas: 4054-67-5

General procedure: A mixture of H2L (0.15 mmol, 0.057 g), phen (0.25 mmol, 0.050 g), Zn(Ac)2·2H2O (0.40 mmol, 0.088 g) and 12 mL H2O was placed in a 25 mL Teflon-lined stainless steel container, heated to 180 C for 72 h,and then cooled to room temperature at a rate of 5 C/h.

The synthetic route of 3,3′,5,5′-Tetramethyl-1H,1’H-4,4′-bipyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Jun; Bai, Chao; Hu, Huai-Ming; Yuan, Fei; Xue, Gang-Lin; Journal of Solid State Chemistry; vol. 249; (2017); p. 87 – 97;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 118430-74-3, name is 3-Cyclopropyl-1-methyl-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H11N3

Example 161 Synthesis of N4-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-9H-pyrimido[4,5-b]indole-2,4-diamine (Cpd. No. 206) Pd2(dba)3 (18 mg) and BINAP (26 mg) were mixed in anhydrous toluene. And the mixture was heated at reflux for 3-4 minutes. This mixture was transferred into a round-bottom flask containing ZBB253 (60 mg), 3-cyclopropyl-1-methyl-1H-pyrazol-5-amine (84 mg), K3PO4 (130 mg), and toluene (2 mL). The mixture was heated at reflux for overnight before quenching with methanol. The reaction mixture was filtered and the mixture was purified by HPLC to yield Cpd. No. 206 as a CF3CO2H salt in 15 mg. ESI-MS calculated for C23H25N8O2 [M+H]+=445.21; Observed: 445.54. 1H NMR (300 MHz, MeOD) delta 7.70 (s, 1H), 7.35 (s, 1H), 6.09 (s, 1H), 3.92 (s, 3H), 3.74 (s, 3H), 2.33 (s, 3H), 2.16 (s, 3H), 1.98-1.88 (m, 1H), 1.03-0.93 (m, 2H), 0.78-0.71 (m, 2H).

The synthetic route of 118430-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37718-11-9, name is 1H-Pyrazole-4-carboxylic acid, 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 37718-11-9, Recommanded Product: 37718-11-9

In a 3L three-necked bottle, 1H-pyrazole-4-carboxylic acid (SM1, 112.0 g, 1.0 mol) and DMF (500 ml) were added and controlled.The system temperature is 0-5°C, and a solution of 254 g (2.0 mol) oxalyl chloride in DMF (500 ml) is slowly added dropwise to the solution of oxalyl chloride in DMF.During the liquid process, the temperature of the control system is maintained at 0-5°C. After the DMF solution of the acyl chloride reagent is added dropwise,Warm to room temperature (25-30°C) and stir for 2h. Then spin to obtain 1H-pyrazole-4-carboxylic acid chloride;

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1H-Pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Xiamen Hailejing Biochemical Co., Ltd.; Qiu Binglin; Chen Huadong; Zhong Baoxiang; Li Jinlin; Huang Zhizheng; (14 pag.)CN107915738; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics