Tag: M.W=0-100

Application of 31230-17-8, A common heterocyclic compound, 31230-17-8, name is 5-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, 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.

S-Ammo-S-methyl-pyrazole-l-carboxylic acid tert-butgammal esterNaH (95percent, 0.57g, 22.7mmol) was added slowly to a 00C solution of 3-Amino-5- methylpyrazole (2.Og, 20.6mmol) in THF (40ml). BoC2O (4.94g, 22.7mmol) was added after 30 min and the mixture was allowed to warm to room temperature. After stirring for 2 h at room temperature, the mixture was poured into a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with CHCI3. The combined organic phases were dried over Na2SO4. Removal of the solvent in vacuum gave a crude mixture of the title compound and its 2-carboxylic acid tert.- butyl ester isomer, which were separated by chromatography on silica in ethyl acetate / heptane 2:1. Yield 2.4g, 59percent.1H-NMR: (400 MHz, D6-DMSO) 5.60 (IH, s), 5.27 (2H, s), 2.34 (3H, s), 1.51 (9H, s); MS (ESI+) = 198.26 (MH-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; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); 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. 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C4H7N3

1 -Methyl- lH-pyrazo 1-3 -amine (158 mg, 1.63 mmol) and DIEA (1.08 mL, 6.52 mmol) was added to a solution of 2-(l-(ter^-butoxycarbonylamino)cyclobutyl)-2-hydroxyacetic acid (400 mg, 1.63 mmol) dissolved in DMF (20 mL). The solution was cooled to 00C and after 10 minutes HATU (620 mg, 1.63 mmol) was added. After approximately 2 hours at RT, LC-MS showed product and no starting material and the solvent was removed by rotary evaporation. The crude product was dissolved in 40 rnL of EtOAc and washed with 25 rnL of sat. NaHCCh (aq). The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude product was purified on a 25 g silica column on a Biotage Flashmaster eluted with a gradient of heptane:ethyl acetate 1 :1, which gave the title compound as a white solid (488 mg, 92percent) yield. [M+H]+ = 325.

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR UK LTD; AYESA, Susana; BELFRAGE, Anna, Karin; CLASSON, Bjoern; GRABOWSKA, Urszula; HEWITT, Ellen; IVANOV, Vladimir; Joensson, Daniel; KAHNBERG, Pia; LIND, Peter; NILSSON, Magnus; ODEN, Lourdes; PELCMAN, Mikael; WAeHLING, Horst; WO2010/70615; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 35344-95-7, 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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of Intermediate 15B (0.50 g, 4.46 mmol) and 6bromo4methoxynicotinonitrile (0.95 g, 4.46 mmol) in dioxane (20 mL) was added K2CO3 (1.54 g, 11.15 mmol) and XANTPHOS (0.52 g, 0.89 mmol) and the resulting reaction mixture was degassed with nitrogen for 5 minutes. Pd2(dba)3(0.41 g, 0.45 mmol) was added and the resulting mixture was degassed again for 5 minutes then heated at 100 °C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite® and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Redisep24 g, 2 2.5 percent MeOH in DCM), to obtain Intermediate 15C (0.40 g, 36.70percent) as a pale yellow solid.1H NMR (400 MHz, DMSOd6) G ppm 2.65 (t, J = 6.78 Hz, 2 H), 3.61 (td, J = 6.78, 5.02 Hz, 2 H), 4.10 (s, 3 H), 4.62 4.76 (m, 1 H), 7.58 (s, 1 H), 7.81 (s, 1 H), 8.47 (s, 1 H), 8.73 (s, 1 H). LCMS (MethodI): retention time 0.83 min, [M+H] 245.3

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (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. 81945-73-5, name is 1H-Pyrazol-1-ol, A new synthetic method of this compound is introduced below., SDS of cas: 81945-73-5

(General Procedure 16)4-Methyl-piperazine-1-carboxylic Acid pyrazol-1-yl Ester The title compound was prepared from 1-hydroxypyrazole and N-methylpiperazine applying the general procedure 16. The crude product was purified by preparative HPLC (water-acetonitrile-0.1% TFA) (17%, salt with TFA). 1H NMR (300 MHz; CDCl3): delta 2.36 (s, 3H), 2.50 (bt, 4H), 3.59 (bs, 2H), 3.71 (bs, 2H), 6.31 (t, 1H), 7.38 (dd, 1H), 7.40 (dd, 1H); HPLC-MS: m/z=211.0 (M+1); Rt=0.40 min.

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; Ebdrup, Soren; de Jong, Johannes Cornelis; Jacobsen, Poul; Hansen, Holger Claus; Vedso, Per; US2003/166644; (2003); 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 81945-73-5 as follows. Formula: C3H4N2O

EXAMPLE 7 6-Imidazolyl-2-(3,5-dimethoxy-s-triazin-1-yloxy)-1-[(1-pyrazolyl)-oxycarbonyl]-benzene 1.75 g (10.8 mmol) of N,N’-carbonylbisimidazole is added to a solution of 1.88 g (10 mmol) of 6-imidazolylsalicylic acid in 30 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes at room temperature, 9.9 mmol of N-hydroxypyrazole is added and the mixture is stirred for a further 14 hours. The reaction mixture is then hydrolyzed with 300 ml of 1N phosphoric acid and the resulting mixture is extracted several times with methyl tert-butyl ether. The organic phases are dried over sodium sulfate and evaporated down under reduced pressure. The residue is taken up in 40 ml of dimethylformamide, and 280 mg of sodium hydride (85% strength in paraffin, 10 mmol) is added. After the mixture has been stirred for 30 minutes at room temperature, 1.58 g (9 mmol) of 1-chloro-3,5-dimethoxy-s-triazine is added and the whole is stirred for 14 hours. The batch is introduced into 300 ml of 0.1N phosphoric acid, and extracted with diethyl ether. The ether phase is dried over sodium sulfate and evaporated down, and the residue is purified by column chromatography.

According to the analysis of related databases, 81945-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF Aktiengesellschaft; US5246914; (1993); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3920-50-1, The chemical industry reduces the impact on the environment during synthesis 3920-50-1, name is Pyrazole-3-carboxaldehyde, I believe this compound will play a more active role in future production and life.

The compound (72.0 mg) obtained in Example 43-1 was dissolved in methanol (3.5 ml) and then added with pyrazole-3-carboxaldehyde (24.5 mg) and sodium cyanoborohydride (35.9 mg). The reaction solution was adjusted to pH 5 with the addition of acetic acid, followed by stirring at room temperature for 14 hours. The reaction solution was added with a 1 mol/l sodium hydroxide aqueous solution and then extracted with chloroform. Then, the organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After the solvent had been distilled off, the residue obtained was purified through silica gel column chromatography (chloroform/ethyl acetate) and treated with hydrochloric acid, thereby obtaining hydrochloride (52.3 mg) of the subject compound as a yellow solid. MS(FAB,Pos.):m/z=486[M+H]+1H-NMR(500MHz,DMSO-d6):delta=0.85(6H,t,J=7.5Hz),1.65(4H,m),2.88(4H,m),3.70(2H,brs),3 .78(2H,brs),4.00(2H,brs),4.10(2H,brs),4.28(2H,brs),6.34(1H,d ,J=2.1Hz),6.65(2H,d,J=8.5Hz),7.21(2H,d,J=8.5Hz),7.32(2H,d,J= 8.3Hz),7.38(2H,d,J=8.3Hz),7.51(2H,s),7.69(1H,d,J=2.1Hz).

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, Pyrazole-3-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Chemical Industry Co., Ltd.; EP1550657; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 930-36-9, A common heterocyclic compound, 930-36-9, name is 1-Methylpyrazole, molecular formula is C4H6N2, 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 stirred solution of 1 -methyl- lH-pyrazole (609 mmol) in dry ether (600 mL) under an atmosphere of nitrogen is added a solution of n-BuLi in hexane (2.6 M, 670 mmol) dropwise at -78C over a period of Ih. The reaction mixture is then stirred at this temperature for a further 1 h, and then dry carbon dioxide gas is passed through the mixture at -78C for 30 min. The reaction mixture is then allowed to warm to room temperature and quenched with water (500 mL). The aqueous phase is separated, washed with ether (500 mL) and cooled to 2-3 0C. To the stirred mixture is added concentrated aqueous hydrochloric acid until a peta of 3 is obtained. The resulting precipitate is collected by filtration, washed with ice-cold water (20 mL), dried first in open air, and then in a vacuum desiccator over P2O5 to afford 2-methyl-2H-pyrazole-3-carboxylic acid as a white powder.[00249] Compound wt: 35.3g, 45.4% yield. 1H NMR (400 MHz, OMSO-d6) delta: 13.31 (IH, bs);7.50 (IH, d); 6.81 (IH, d); 4.07 (3H, s).

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; Galapagos NV; WO2009/71705; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 28466-26-4, 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. 28466-26-4, name is 4-Aminopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

0.2g of compound 2 and 0.11g of 4-aminopyrazole were dissolved in n-butanol. 0.27g of N,N-diisopropylethylamine was added to the solution and was heated at 150C under microwave for 2h. After completion of the reaction, the solvent was evaporated to dryness using a rotary evaporator under reduced pressure to obtain a crude product. The product was purified by column chromatography (dichloromethane:methanol = 20:1) to give 0.15g of compound 3 as a yellow solid, yield: 65%.

The synthetic route of 4-Aminopyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-26-4, These common heterocyclic compound, 28466-26-4, name is 4-Aminopyrazole, 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.

A mixture of N-(2-chloropyrimidin-4-yl)-l-isopropyl-lH-imidazo[4,5-c]pyridin-6-amine (Example 12, Step 4) (51.1 mg, 0.177 mmol), lH-pyrazol-4-amine (23.9 mg, 0.288 mmol), trifluoroacetic acid (10.0 mu^, 0.129 mmol) and fert-butanol (1.5 mL, 16 mmol) was heated in a sealed vial at 100 C for 2 days. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated in vacuo. The crude product (20.3 mg) was purified via reverse-phase HPLC and lyophilized to yield 4.6 mg (8%) of the title compound. LCMS (ESI): RT (min) = 3.051, [M+H]+ = 336.2, method = B; lH NMR (400 MHz, DMSO-d6) delta 12.43 (s, 1H), 9.72 (s, 1H), 8.83 (s, 1H), 8.66 (d, J = 1.0 Hz, 1H), 8.38 (s, 1H), 8.01 (d, J = 5.7 Hz, 1H), 6.67 (s, 1H), 4.62 (br s, 1H), 1.51 (d, J = 6.6 Hz, 6H).

Statistics shows that 4-Aminopyrazole is playing an increasingly important role. we look forward to future research findings about 28466-26-4.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; HANAN, Emily; HEFFRON, Timothy; PURKEY, Hans; ELLIOTT, Richard Leonard; HEALD, Robert; KNIGHT, Jamie; LAINCHBURY, Michael; SEWARD, Eileen M.; WO2014/81718; (2014); 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. 28466-26-4, name is 4-Aminopyrazole, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 28466-26-4

Compound 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (206 mg, 1 mmol),1H-pyrazole-4-amine (83mg, 1mmol),Diisopropylethylamine (258mg, 2mmol)Mix with ethanol (20 mL), heat to 80 C and stir for 2 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane / methanol = 19/1).The target product 4-((1H-pyrazol-4-yl) amino) -6-chloropyridazine-3-carboxylic acid methyl ester 41a (150 mg, yellow solid) was obtained,Yield: 59%.

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 28466-26-4.

Reference:
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics