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. 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H5ClF2N2O

In a 500 ml flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde are added to 30 ml of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 ml of water is added to the reaction mixture, followed by 103 ml of a 30% solution of hydrogen peroxide in water, whilst keeping the temperature below 37 C. After the end of the addition, the reaction mixture is stirred at 50 C. for 7 hours. Once the reaction mixture is back to room temperature, the two phases are separated and the organic phase is extracted with 100 ml of water. The combined aqueous phases are acidified to pH 2 with aqueous hydrochloric acid. The resulting white precipitate is filtered, washed twice with 20 ml of water, and dried to yield 3.2 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm: 3.78 (s, 3H); 7.12 (t, 1H, JHF=53.60 Hz); 13.19 (s, 1H); IR (KBr): 1688 cm-1 (C=O); 2200-3200 cm-1 broad (hydrogen bond).

According to the analysis of related databases, 660845-30-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Benting, Jurgen; Cristau, Pierre; Desbordes, Philippe; Gary, Stephanie; Greul, Jorg; Helmke, Hendrik; US2013/210864; (2013); 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. 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 42027-81-6

A solution of 4-nitro-lH-pyrazole (l .Og, 8.85mmol), potassium carbonate (2eq) and 2- bromoethanol (l . leq) in acetonitrile (30mL) was heated at 60C for 18h. After cooling to rt the mixture was diluted with EtOAc and washed with H20. The organic phase was collected, dried (hydrophobic frit) and concentrated in vacuo. The crude residue was dissolved in ethanol (30mL), palladium on carbon (50mg) was added and the reaction was stirred under a balloon of hydrogen for 18h. The resulting mixture was filtered through Celite and the filtrate concentrated in vacuo to give 2-(4-amino-lH-pyrazol-l-yl)ethanol

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLZOME LIMITED; OXENFORD, Sally; HOBSON, Andrew; OLIVER, Kathryn; RATCLIFFE, Andrew; RAMSDEN, Nigel; WO2013/17479; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference 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.

To a solution of 2,5,6-trichloronicotinonitrile (Method 44, 1.0 g, 4.8 mmol) and DIEA (0.81 g, 6.2 mmol) in n-BuOH (5 ml) was added S-cyclopropyl-lH-pyrazol-S-amme (2.3 g, 19.3 mmol). The reaction was heated to 60 0C for 2 hours, at which point the reaction was cooled to room temperature and concentrated. The resulting residue was diluted with 10 ml ACN, and stored at 00C for 1 hour. The solids that formed were then filtered, washed with cold ACN, dried and collected to give the title compound (0.62 g, 43%). MS: Calcd.: 294; Found: [M+H]+ 295.

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 821767-61-7, The chemical industry reduces the impact on the environment during synthesis 821767-61-7, name is tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, I believe this compound will play a more active role in future production and life.

Example 15 tert-butyl 4-formyl-1H-pyrazole-1-carboxylate (1.0 g) and (6-isopropylpyridin-3-yl)amine (0.694 g) were dissolved in 1,2-dichloroethane (25 mL), acetic acid (0.29 mL) and sodium triacetoxyborohydride (2.16 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give tert-butyl 4-{[(6-isopropylpyridin-3-yl)amino]methyl}-1H-pyrazole-1-carboxylate (1.46 g). 1H-NMR(CDCl3)delta: 1.26(6H,d,J=6.9Hz), 1.65(9H,s), 2.96(1H,sept,J=6.9Hz), 3.80-3.90(1H,m), 4.23(2H,d,J=6.0Hz), 6.88(1H,dd,J=3.0,8.4Hz), 6.99(1H,d,J=8.4Hz), 7.70(1H,s), 8.01(1H,d,J=3.0Hz), 8.04(1H,s).

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, tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1852431; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA·H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 113100-53-1, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C6H5F3N2O2, 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. Quality Control of 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid

e) 1-methyl-3-trifluoromethyl-lH-pyrazole-4-carboxylic acid (2.5g, 13mmol) was dissolved in dichloromethane (25ml) containing 5 drops of N,N-dimethylformamide. A solution of oxalyl chloride (1.8g, 14mmol) in dichloromethane (5ml) was added dropwise at room temperature. This mixture was stirred for 2hours at the same temperature and was subsequently slowly added to a mixture of 2-[5-(3,3-dimethyl-but-1-ynyl)-thiophen-2-yl]- phenylamine (3.3g, 13mmol) and triethylamine (2.0g, 20mmol) in dichloromethane (30ml). After stirring the reaction mixture for 8hours at room temperature, it was poured on ice and extracted with dichloromethane. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated. The remaining oil was purified by silica gel chromatography using ethyl acetate and hexane as eluents, giving Compound No. lai.098 (1.2g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 113100-53-1, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2005/123722; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 478968-48-8, 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 478968-48-8 as follows.

A mixture of Cul (88 mg, 0.46 mmol, 0.10 equiv), L-proline (108 mg, 0.94 mmol, 0.20 equiv), potassium carbonate (1.3 g, 9.41 mmol, 2.00 equiv), ethyl 3-methoxy-li7-pyrazole-4-carboxylate (800 mg, 4.70 mmol, 1.00 equiv), and 5-bromo-2-(trifluoromethyl)pyrimidine (1.28 g, 5.64 mmol, 1.20 equiv) in DMSO (5 mL) was stirred overnight at 100 C under nitrogen. The reaction mixture was diluted with 40 mL of water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1 :5) to afford the title compound (580mg, 39%) as a white solid.

According to the analysis of related databases, 478968-48-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; VERMA, Vishal; SHORE, Daniel; VOLGRAF, Matthew; ESTRADA, Anthony A.; LYSSIKATOS, Joseph; (153 pag.)WO2018/15410; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 20154-03-4, 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. 20154-03-4 name is 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.

Step 1: Preparation of 4-iodo-3-(truoromethyl)-1H-pyrazole. To a solution of 3- (trifluoromethyl)-1H-pyrazole (500 mg, 3.7 mmol) in 50percent 112S04 at 0 °C was added MS (992 mg, 4.4 mmol). The suspension was stirred at 0°C for 10 mm and then at r.t. for 3 hr. The resulting mixture was quenched with water (50 mL), and then stirred overnight. The precipitate was collected by filtration and dried to afford 4-iodo-3-(trifluoromethyl)-1H-pyrazole.LC-MS:m/z 263 (M+H).

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

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); 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 52222-73-8 as follows. SDS of cas: 52222-73-8

Intermediate (1): (4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methanol A mixture of (4-iodophenyl)methanol (1030 mg, 4.41 mmol), 4-(trifluoromethyl)-1H-pyrazole (600 mg, 4.41 mmol), copper (I) iodide (168 mg, 0.882 mmol), trans-4-hydroxy-L-proline (231 mg, 1.76 mmol) and cesium carbonate (2900 mg, 8.82 mmol) in dimethylsulfoxide (7.5 mL) was heated to 85 C. for 20 hours. The mixture was diluted with water and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-45% ethyl acetate in heptane), gave (4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methanol. 1H NMR (400 MHz, CDCl3, delta): 8.16 (s, 1H), 7.89 (s, 1H), 7.65 (d, J=8.39 Hz, 2H), 7.47 (d, J=8.39 Hz, 2H), 4.74 (d, J=5.66 Hz, 2H), 1.85 (t, J=5.86 Hz, 1H).

According to the analysis of related databases, 52222-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; US2012/202834; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 89088-55-1, 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. 89088-55-1, name is 5-Bromo-1-methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (158 mg, 0.68 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.14 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.06 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50 C. Then 5-bromo-1-methyl-1H-pyrazol-3-amine (120 mg, 1 equiv) was added, and stirred for 18 h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3(10 mL) and with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and ready to use in step-2.

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, 5-Bromo-1-methyl-1H-pyrazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics