Tag: M.W:100-200

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. 14521-80-3, name is 3-Bromo-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-1H-pyrazole

A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 mL of N,N-dimethylformamide was stirred at 100C for 8 hours. After cooling to room temperature and adding water, the reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

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; Sumitomo Chemical Company, Limited; EP2145885; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic 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. HPLC of Formula: C5H4N2O4

Step 1; To a solution of Compound 14 (60 g, 345 mmol) in methanol (600 mL), under flow of nitrogen, thionyl chloride (75 mL, 1034 mmol) was added at 0C. The solution was then heated at reflux for 4 hours. The reaction mixture was concentrated in vacuo to yield crude product 15 (64.3 g). LC/MS (Method A): 0.93 min, [M+H]+ = 185.

The synthetic route of 1H-Pyrazole-3,5-dicarboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; EP2426135; (2012); A1;,
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. 31728-75-3, name is 1,5-Dimethyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

To a suspension of 6-(2-amino-5-chlorothiazol-4-yl)-3,4-dihydroquinolin-2(1H)-one (0.100 g, 0.41 mmol) and 1,5-dimethyl-1H-pyrazole-4-carboxylic acid (0.063 g, 0.22 mmol), and DIPEA (0.16 mL, 0.51 mmol in acetonitrile (5 mL) in a sealed tube was added propylphosphonic anhydride solution (50 wt % in ethyl acetate, 0.61 mL, 0.1.02 mmol). The sealed tube was heated to 100 C. for 16 h. The resulting mixture was cooled to room temperature, and partitioned between EtOAc (50 mL) and 50 mL of water. The organic layer was separated and the aqueous layer was extracted with EtOAc (3*25 mL). The combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography by 0-5% methanol-dichloromethane to give 1,5-dimethyl-N-(4-(2-oxo-1,2,3,4-tetrahydroquinol in-6-yl)thiazol-2-yl)-1H-pyrazole-4-carboxamide (0.044 g, 30%). 1H NMR (400 MHz, DMSO-d): delta 12.21 (bs, 1H), 10.18 (s, 1H), 8.30 (s, 1H), 7.74 (m, 1H), 7.69 (dd, 1H, J=8.4, 2.0 Hz), 7.44 (s, 1H), 6.90 (d, 1H, J=8.0 Hz), delta, 3.77 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 2.91 (s, 3H), 2.50 (partial masked under d-DMSO, m, 2H); MS (ESI): Calcd. For C18H17N5O2S: 367, found 368 (M+1)+.

According to the analysis of related databases, 31728-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nantbio, Inc.; Tao, Chunlin; Nallan, Laxman; Ho, David G.; Wang, Qinwei; Weingarten, Paul; Juncker-Jensen, Anna B.; (121 pag.)US2018/201610; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5334-40-7, 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. 5334-40-7 name is 4-Nitro-1H-pyrazole-3-carboxylic 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.

4-nitropyrazole-3-carboxylic acid (2.5 g; 15.9 mmol) was added to a stirred solution of aniline (1.6 mL; 17.5 mmol), EDC (3.7 g; 19.1 mmol), and HOBt (2.6 g; 19.1 mmol) in N,N-dimetnylformamide (DMF) (25 ml), then stirred at room temperature overnight.The solvent was removed by evaporation under reduced pressure and the residue triturated with ethyl acetate/saturated NaHCO3 solution.The resultant solid was collected by filtration, washed with water and diethyl ether then dried under vacuum to give 2.85 g of the t itle compound (sodium salt) as a yellow/brown solid.(LC/MS: Rt 2.78, [M+H]+ 232.95).

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

Reference:
Patent; ASTEX TECHNOLOGY LIMITED; WO2005/12256; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-45-8, name is 4-Bromo-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 2075-45-8, HPLC of Formula: C3H3BrN2

To a solution of 4-bromopyrazole (10.0 g, 68.0 mmol) in N,N-dimethylformamide (100 mL) was added dropwise triethylamine (23.7 mL, 170 mmol) under nitrogen atmosphere at room temperature. Trityl chloride (37.9 g, 136 mmol) was added to the reaction solution on an ice bath (0 C.), and stirred for 3 hours at 70 C. Water (400 mL) was added to the reaction solution to precipitate the solids. The precipitated solids were filtered and dried under a reduced pressure. The solids were then azeotropically dried with toluene to obtain the title compound (22.9 g, 87%). 1H-NMR Spectrum (DMSO-d6) delta (ppm): 7.04-7.07 (6H, m), 7.35-7.38 (9H, m), 7.52 (1H, d, J=0.4 Hz), 7.76 (1H, d, J=0.8 Hz).

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; Eisai R&D Management Co., Ltd.; US2007/105904; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3469-69-0, A common heterocyclic compound, 3469-69-0, name is 4-Iodopyrazole, molecular formula is C3H3IN2, 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.

General procedure: Step 1: 1-methyl-4-iodopyrazole 1H-4-iodopyrazole (20 g), potassium carbonate (28.45 g) and acetone (120 mL) were added into a round bottomed flask (250 mL) and agitated for 10 min. Then iodomethane (17.56 g) was added and the mixture was agitated at room temperature over night. After that, the mixture was filtrated and concentrated, the residue was recrystallized from n-hexane to prodce 1-methyl-1H-4-iodopyrazole (15 g) as white acicular crystal. 1H-NMR (300Hz, CDCl3) delta: 7.48 (s, 1H), 7.40 (s, 1H), 3.92 (s, 3H).

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

Reference:
Patent; Shanghai Institute Materia Medica, Chinese Academy Of Sciences; DUAN, Wenhu; GENG, Meiyu; CHEN, Fang; AI, Jing; CHEN, Yi; ZHAN, Zhengsheng; LV, Yongcong; WANG, Ying; DING, Jian; EP2650293; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27258-32-8, name is 1-Methyl-1H-pyrazole-3-carbaldehyde, 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 27258-32-8, Recommanded Product: 1-Methyl-1H-pyrazole-3-carbaldehyde

in room temperature, Mix 1-methyl-1H-pyrazole-3-carbaldehyde (11.0 g, 0.1 mol), sodium bromate (4.5 g, 0.03 mol) and 100 g of acetic acid (1.67 mol), add 25 g of ammonia-containing molecular mass concentration 25percent ammonia water and 400 ml water, heated to 90 ° C, the reaction exotherm, maintain the reaction temperature 100 ° C, reflux reaction for 1 hour until 1-methyl-1H-pyrazole-3-carbaldehyde reaction is complete, the reaction solution is cooled to room temperature Pour into ice water to quench and dilute, neutralize until the reaction solution is neutral, extract with ethyl acetate, dry, concentrate the product, distill it under reduced pressure and recrystallize to obtain 8.6 g of product, yield 80percent, purity 98percent the above.

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

Reference:
Patent; Changsha Luxing Biological Technology Co., Ltd.; Tan Yongjun; (14 pag.)CN108707113; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 34605-66-8, These common heterocyclic compound, 34605-66-8, name is 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-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.

At -78 , 3- (2,5-dimethyl -1H- pyrrol-1-yl) -1-methyl -1H- pyrazole (708.5mg, 4.04mmol) in THF (8mL)Was added dropwise a solution of n-BuLi (2.4M in tetrahydrofuran, 2.5mL, 6.0mmol). The reaction system was stirred for 0.5 hours maintaining -78 , then0 moved after two hours while stirring. Acetone was added to the system (362.1mg, 6.24mmol), the resulting mixture was stirred at room temperature for 3Hours, then water (20 mL) to quench the reaction, and (50mL × 3) and extracted with ethyl acetate. The combined organic phases with saturated brine (50mL of), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (EtOAc / PE (v / v) = 1/5) of pureOf the title compound as a yellow oil (353.0mg, yield 37.4%).

The synthetic route of 34605-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Xi, Ning; Li, Minxiong; Li, Xiaobo; Dai, Weilong; Hu, Haiyang; Zhang, Tao; Chen, Wuhong; (105 pag.)CN105461694; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51985-95-6, name is Methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H8N2O3, 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. COA of Formula: C6H8N2O3

Example 134; (S, E)-Methyl 4-(6-(l-(3-(5-chloro-2-(1H-tetrazol-1-yl)phenyl)acrylamido)-2-(5- methoxy-1-methyl-1H-pyrazol-3-yl)ethyl)-3-oxo-2>3-dihydropyridazin-4- yl)phenylcarbamate; 134 A. methyl 5 -methoxy-1 -methyl- 1H-pyrazole-3-carboxylate: To a cooled solution (0 °C) of methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate (1.60 g, 10.25 mmol) and K2CO3 (2.124 g, 15.37 mmol) in DMF (10 mL) was added dropwise MeI (0.703 mL, 11.27 mmol). The reaction mixture was stirred under argon at rt for 5 days. The reaction mixture was diluted with EtOAc, washed with H2O (1 x 15 mL), saturated NaHCO3 (1 x 15 mL) and brine (1 x 15 mL). The organic phase was dried over MgSO^ filtered an Purification by normal phase chromatography gave 134A (1.20 g, 7.05 mmol, 68.8 percent yield) as a white solid. LC- MS (ESI) m/z: 171.2(M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51985-95-6, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/114677; (2009); A1;,
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. 3994-50-1, name is 1-Methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Methyl-4-nitro-1H-pyrazole

General procedure: To a 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

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 3994-50-1.

Reference:
Article; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics