Tag: M.W:200-300

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. 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H7ClN4

General procedure: In a round bottomed flask of 100 mL equipped with a condenser we added a solution of 2-substituted-3-aminopyrrole-4-carbonitrile 4 (1 mmol) with either cyclopentanone or cyclohexanone (1.4 mmol) in 30 mL of distilled 1,2-dichloroethane.Anhydrous AlCl3 (4 mmol) was then added, and the mixturewas refluxed for 30 and 32 min, respectively, under microwaveirradiation (at a constant power of 400 W). The mixture wasthen cooled to room temperature. After cooling a mixture oftetrahydrofurane and water (1 : 1, 20 mL) was added, followedby the drop wise addition of NaOH (aq. solution 10%) untilthe solution was basic. After this, the mixture was stirred for30 min, and extracted with dichloromethane (3×20 mL). Thecombined extracts were washed with saline (20 mL), driedover MgSO4, filtered, and the solvent evaporated to obtain asolid, which was identical in all respects with that obtainedfrom the thermal method (mp, TLC, NMR).

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 51516-67-7.

Reference:
Article; Alshareef, Hossa Fahad; Mohamed, Heba Abd El Hady; Salaheldin, Abdellatif Mohamed; Chemical and Pharmaceutical Bulletin; vol. 65; 8; (2017); p. 732 – 738;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 92525-10-5, 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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of the ail above brown solid, Pd(PPh3 )2Cl2 (31 mg, 0.044 mmol) and Cu l (8 mg, 0.044 mmol) in DMF (2 mL) under N2 atmosphere was added a solution of 3-iodo-l – methyl- 1 f-pyrazole (170 mg, 0.817 mmol) and triethylamlne (179 mg, 1.77 mmol) in DMF (1 .5 mL), The resulted mixture was heated to 80 C and stirred further for 16 hours, then diluted with EtOAc (20 mL) and washed with water (20 mL x 2) and brine (20 mL). The separated organic phase was concentrated in vacuo and the residue was suspended in a mixture of PE/EtOAe (5/1 (v/v), 12 mL). The mixture was stirred at rt for 4 hours, then filtered and the filter cake was washed with PE (10 mL). The filter cake was dried in vacuo to give the title compound as an orange-yellow solid (139 mg, yield for two steps (Step 4 and Step 5): 72.8%). MS (ESI, pos. ion.) m/z: 234.1 [M+H]+; FontWeight=”Bold” FontSize=”10″ H NMR (400 MHz, DMSO-Lambda) delta (ppm): 8.22 (s, 1H), 7.79 (d, J = 2.2 Hz, 1H), 6.64 (d, J = 2.2 Hz, 1H), 3.89 (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, 3-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.; XI, Ning; WANG, Liang; WANG, Tingjin; WU, Weibin; (123 pag.)WO2015/175579; (2015); 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. 15001-11-3, name is Ethyl 5-amino-1-(p-tolyl)-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H15N3O2

General procedure: Intermediate 4 (0.001mol) and 5 (0.001mol) were dissolved in pyridine, phosphorus oxychloride is slowly added dropwise under ice bath conditions, then at 40-60C reacted for 5-8h. Finally, the mixture was poured into 30mL saturated Na2CO3 solution and stirred well. After the mixture was acidified, the saturated CuSO4 solution was used to remove pyridine, which greatly improved the purity and yield of the product. The data for compounds 8I-8VI are provided in the supporting information.

The synthetic route of 15001-11-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hao; Ren, Zi-Li; Wang, Wei; Gong, Jie-Xiu; Chu, Ming-Jie; Ma, Quan-Wei; Wang, Jie-Chun; Lv, Xian-Hai; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 81 – 87;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89607-15-8, 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. 89607-15-8, name is 3-Bromo-1-methyl-4-nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

Step 4: Into a 25 mL round bottom flask containing a solution of 3-bromo-1-methyl-4-nitro-1H- pyrazole (1.0 g, 5 mmol) in toluene (5 mL) were added tributyl(vinyl)tin (1.7 mL, 58 mmol) andtetrakis(triphenylphosphine)palladium(0) (300 mg, 0.25 mmol) and the reaction was heated at120 C for 6 h. The reaction mixture was cooled to room temperature, concentrated and purifiedby flash chromatography eluting with ethyl acetate in petroleum ether (15-20%) to afford 1-methyl-4-nitro-3-vinyl-1H-pyrazole as a solid. ?H NMR (CDC13, 300 MHz): 8.07 (s, 1H), 7.22(dd,J= 17.6, 11.2 Hz, 1H), 6.19 (dd,J= 17.7, 4.6 Hz, 1H), 5.54(dd,J= 11.1, 1.6 Hz, 1H), 3.97(s, 3H).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-1-methyl-4-nitro-1H-pyrazole. 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.; (187 pag.)WO2016/144846; (2016); 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 139308-52-4 as follows. Safety of Ethyl 3-bromo-1-methyl-1H-pyrazole-4-carboxylate

[1042] a mixture of compound 163c (2 g, 8.58 mmol), meb(oh)2 (2.05 g, 34.3 mmol), pd(pph3)4 (793 mg, 687 umol), K2CO3 (2.37 g, 17.2 mmol) in dioxane (50 ml) and H2O (10 ml) was degassed and purged with n2 for 3 times, and then the mixture was stirred at 120 C for 12 hour under N2 atmosphere. The reaction mixture was extracted with ethyl acetate 50 ml (50 ml x 2). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate = 100: 1 to 80: 1). Compound 408a (1.4 g, yield: 97.0%) was obtained as a yellow solid. 1H NMR (400mhz, CDCl3) delta 7.87 – 7.73 (m, 1h), 4.27 (q, j = 7.1 hz, 2h), 3.91 -3.75 (m, 3h), 2.51 – 2.40 (m, 3h), 1.33 (t, j = 7.1 hz, 3h).

According to the analysis of related databases, 139308-52-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51516-67-7, A common heterocyclic compound, 51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7ClN4, 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: A mixture of theintermediate compounds 2 (1 mmol) and 3 (1 mmol) in ethanol(10 mL) was stirred at reflux for 2 h. After cooling to roomtemperature, the precipitated solid was filtered, and thenrecrystallized from ethanol to give the title compounds 5a-5p.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

INTERMEDIATE 4; Step A: fert-Butyl 2-(2-aniino-2-oxoemyl)-2,6-dihvdropvrrolof3,4-c|pyrazole-5(4H)- carboxylateA 2 L three neck flask fitted with a thermometer, a mechanical stirrer and an addition funnel was charged with a suspension of tert-butyl 2,6-dihydropyrrolo[3,4-c]pyrazole- 5(4H)-carboxylate (18.01 g, 86.5 mmol) in anhydrous acetonitrile (1.0 L). Sodium hydride (60% dispersion in oil, 4.15 g, 104 mmol) was added to the suspension in one portion under nitrogen. The reaction was stirred at room temperature for 2 h. The resulting white suspension was then cooled in an ice bath and iodoacetamide (31.95 g, 173 mmol) was added. The ice bath was then removed and the mixture was stirred 18 h at room temperature. The mixture was quenched with water (50 mL) and the solvent was removed under reduced pressure. The residue was partitioned between diluted NaCl (50 mL brine and 100 mL water) and 1.0 L EtOAc. The aqueous layer was extracted with 2 1.0L EtOAc. The organic layers were combined and dried over Na2S04 and solvent was evaporated under reduced pressure. Crude material was purified on silica gel eluting with 20-50%EtOAc/CH2Cl2 to wash out excess iodoacetamide, and then with 2- 10%MeOH CH2Cl2 to afford a mixture of the two products which were separated on a chiral AD column by eluting with 30% MeOH/C02 to afford the title compound (less mobile fraction). LC- MS – 267.32 [M+l].

According to the analysis of related databases, 1280210-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WILKENING, Robert, R.; APGAR, James, M.; BIFTU, Tesfaye; FENG, Danqing; QIAN, Xiaoxia; WEI, Lan; WO2011/103256; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, molecular formula is C7H11BrN2, 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 70951-85-8

A mixture of 4-bromo-1-tert-butyl-1H-pyrazole (3.3 g, 16.3 mmol), bis(pinacolato)diboron (8.3 g, 32.6 mmol), PdCl2(dppf) (1.8 g, 2.4 mmol), and KOAc (3.2 g, 32.6 mmol) in 1,4-dioxane (60 mL) was heated at reflux for 15 hours. After the completion of the reaction, the mixture was filtered and the filter cake was washed with EtOAc (100 mL). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography using heptane/ethyl acetate (10% to 50%) as eluting solvents to afford 1-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as white solid (1.0 g, 25%). MS (ESI) m/z: 251 [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 70951-85-8, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing; WO2014/1377; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1222174-92-6, name is Methyl 5-bromo-1-methyl-1H-pyrazole-3-carboxylate, molecular formula is C6H7BrN2O2, 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. Recommanded Product: 1222174-92-6

A solution of intermediate 2a (500 mg), 2-(trifluoromethyl)beneneboronic acid (650 mg), PEPPSI-Ipr (77 mg) and potassium carbonate (939 mg) in dioxane (10 mL) were heated to 120 C. for 18 h. The mixture was chilled, filtered and the volatiles were removed under reduced pressure. The residue was purified by chromatography (Interchim cartridge50SiHP/12 g, Cy/EtOAc) to yield the desired compound (55% yield). [0378] LC-MS (Method 2): m/z [M+H]+=285.2 (MW calc.=284.23); Rt=0.83 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1222174-92-6, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 84547-84-2, 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. 84547-84-2 name is 4-Bromo-1-methyl-1H-pyrazole-5-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.

A mixture of 4-bromo- 1 -methyl – 1 //-pyrazole-5-carboxylic acid (4.80 g, 23.4 mmol, CAS 84547-84-2) in THF (40.00 mL) was added BH3/THF (93.60 mL, 1 M). The mixture was stirred at 80 C for 12 hours under N2 atmosphere. To the mixture was added EtOAc (200 mL). The mixture was washed with saturated NaHCO, (200 mL x 3). The organic layer was dried over anhydrous Na2S04, filtered and concentrated to give a residue. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 100 : 0 to 100 : 10) to give (4-bromo-l -methyl- li-pyrazol-5-yl)methanol (4.10 g, 92% yield) as a white solid. 1HNMR (400 MHz, DMSO-6): d 7.26 (s, 1H), 4.62 (s, 2H), 3.86 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics