Day: June 7, 2021

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. 863548-52-1, name is (1-Methyl-1H-pyrazol-5-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (1-Methyl-1H-pyrazol-5-yl)methanamine

General procedure: N,N-Diisopropylethylamine (3.0-4.0 eq) was added to 8-methoxyquinoline-3-carboxylic acid (1.0 eq) in solvent (dichloromethane, tetrahydrofuran,or N,N-dimethylformamide, 0.05 to 0.2 M) at room temperature. Then, 1-((dimethylamino)(dimethyliminio)methyl)-1H-[1,2,3]triazolo[4,5-b]pyridine 3-oxide hexafluorophosphate(V)(1.0-1.5 eq) was added and the reaction mixture was stirred for five minutes. Then, amine (1.0 – 2.0 eq) was added and the reaction mixture was stirred for one to sixteen hours. 10% Aqueous citric acid was added and the reaction mixture was extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over magnesium sulfate, filtered,and concentrated. The resulting residue was purified by RP HPLC or silica gel chromatography to give the quinoline-3-carboxamide (1%-95% yield).

According to the analysis of related databases, 863548-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Deaton, David N.; Do, Young; Holt, Jason; Jeune, Michael R.; Kramer, H. Fritz; Larkin, Andrew L.; Orband-Miller, Lisa A.; Peckham, Gregory E.; Poole, Chuck; Price, Daniel J.; Schaller, Lee T.; Shen, Ying; Shewchuk, Lisa M.; Stewart, Eugene L.; Stuart, J. Darren; Thomson, Stephen A.; Ward, Paris; Wilson, Joseph W.; Xu, Tianshun; Guss, Jeffrey H.; Musetti, Caterina; Rendina, Alan R.; Affleck, Karen; Anders, David; Hancock, Ashley P.; Hobbs, Heather; Hodgson, Simon T.; Hutchinson, Jonathan; Leveridge, Melanie V.; Nicholls, Harry; Smith, Ian E.D.; Somers, Don O.; Sneddon, Helen F.; Uddin, Sorif; Cleasby, Anne; Mortenson, Paul N.; Richardson, Caroline; Saxty, Gordon; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1456 – 1478;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25016-11-9, name is 1-Methyl-1H-pyrazole-4-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 25016-11-9, Product Details of 25016-11-9

To a 22 L 3-neck RB flask in an ambient temperature water bath was charged with 7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine monosulfate 6 (400 g, 1.38 mol) and sodium acetate (237 g, 2.89 mol) as solids, followed by 5 L MeOH. 1-methyl-1H-pyrazole-4-carbaldehyde (176 g, 1.60 mol) was then added in a single portion. The mixture was stirred for ~1 h, before the addition of sodium cyanoborohydride (143 g, 2.27 mol) in three portions over 15 min. After 2 h, additional sodium cyanoborohydride (13 g) was added, and it was stirred for another 4 h. Sarcosine (19 g, 0.21 mol) was then added and it was stirred at rt overnight. The solution was cooled to ~10 C, before the addition of 8 L water over 0.5 h while cooling in an ice bath. Then 2.5 L of 2N NaOH solution was added over 2.5 h (pH > 12). Additional 1.5 L water was added in a single portion. It was cooled in an ice bath and stirred overnight. The precipitate was collected by filtration, washed with water (2 x 1 L), and dried in vacuum at 50-60 C to afford the title compound (381.7 g, 97%). 1H NMR (500 MHz, d6-DMSO) d ppm 2.49-2.53 (m, 4H), 2.96-2.99 (m, 4H), 3.28 (s, 2H), 3.78 (s, 3H), 7.28 (s, 1H), 7.38 (d, J = 8.0 Hz, 1H), 7.54 (s, 1H), 7.95-7.80 (m, 2H).

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

Reference:
Article; Xiong, Hui; Wu, Ye; Lehr, Scott G.; Blackwell, William; Steelman, Gary; Hulsizer, Jim; Urbanek, Rebecca A.; Tetrahedron Letters; vol. 53; 44; (2012); p. 5833 – 5836,4;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 948570-75-0, name is 1-(2-Methoxyethyl)-4-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 948570-75-0, COA of Formula: C6H9N3O3

The 1 – (2 – methoxy ethyl) -4 – nitro – 1H – pyrazole (5 g, 29.21 mmol) dissolved in ethanol (25 ml) and ethyl acetate (25 ml) in, add Raney nickel (500 mg), under the hydrogen environment reaction 5 hours. Diatomite filter, evaporating the filtrate, a brown solid 3.6 g, yield 87%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Methoxyethyl)-4-nitro-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Seth Ming Qiang Pharmaceutical Technology Co., Ltd.; Zhang Qiang; Liu Yansheng; Li Xingfu; Hu Chenming; (96 pag.)CN109535132; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 26621-44-3, 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. 26621-44-3 name is 3-Nitro-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.

To a mixture of 3-nitro-1H-pyrazole (10 g, 88.44 mmol) in DMF (80 mL) was added NaH (4.24 g, 106.13 mmol, 60% purity) in portions at 0 C. Then to the mixture was added SEM-Cl (17.69 g, 106.13 mmol, 18.78 mL) dropwise at 0C. The mixture was stirred at 25 C for 1 h. The resulting mixture was diluted with water and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL×3), 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=1:0 to 5:1, Rf = 0.7,0.75) to provide the title compound (29.5 g, crude) as a yellow oil.

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

Reference:
Patent; KADMON CORPORATION, LLC; LIU, Kevin G.; OLSZEWSKI, Kellen L.; KIM, Ji-In; POYUROVSKY, Masha V.; MORRIS, Koi; YU, Xuemei; LAMARQUE, Christophe; (0 pag.)WO2020/5935; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 29097-00-5, A common heterocyclic compound, 29097-00-5, name is Methyl 3-amino-1H-pyrazole-4-carboxylate, molecular formula is C5H7N3O2, 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 solution of 5-aminopyrazole 5g (1 mmol) and ynone 7 (1 mmol) inMeOH (1 mL) was added dropwise to a mixture of AcOH (0.5 mL) andwater (10 mL) and the mixture was stirred at r.t. for 7 days. The productwas extracted by CH2Cl2 (3×25 mL) and the combined organic phaseswere dried over anhydrous Na2SO4, filtered, and the filtrate was evaporatedin vacuo. The residue was purified by CC (EtOAc/hexanes).Fractions containing the product were combined and evaporated invacuo to give 10.

The synthetic route of 29097-00-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Petek, Nejc; ?tefane, Bogdan; Novinec, Marko; Svete, Jurij; Bioorganic Chemistry; vol. 84; (2019); p. 226 – 238;,
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. 35100-92-6, name is 1,5-Dimethyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

Example 65 Synthesis of N-(1,5-Dimethyl-1H-pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine (Cpd. No. 115) Pd2(dba)3 (27 mg, 0.03 mmol) and BINAP (37 mg, 0.06 mmol) were mixed in anhydrous toluene (5 mL). The mixture was heated at reflux for 3-4 minutes. This clear, orange-red color solution was transferred into a round-bottom flask containing S13 (102 mg, 0.3 mmol), 1,5-dimethyl-1H-pyrazol-3-amine (70 mg, 0.6 mmol), K3PO4 (212 mg, 1.0 mmol), and anhydrous toluene (5 mL). The mixture was heated at reflux for overnight before quenching with methanol. The reaction mixture was filtered through a pad of Celite and the organic layer was collected, concentrated, and purified by HPLC to yield Cpd. No. 115 in 31 mg as a CF3CO2H salt. 1H NMR (300 MHz, MeOD-d4): 8.24 (s, 1H), 7.46 (s, 1H), 6.25 (s, 1H), 3.98 (s, 3H), 3.90 (s, 3H), 2.84 (s, 3H), 2.39 (s, 3H), 2.33 (s, 3H), 2.16 (s, 3H). ESI-MS calculated for C22H24N7O2 [M+H]+=418.20, Observed: 418.50.

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 35100-92-6.

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: 16461-94-2, name is 4-Bromo-1H-pyrazol-3-amine, 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 16461-94-2, Quality Control of 4-Bromo-1H-pyrazol-3-amine

Step 2 :4-(3-Bromopyrazolori,5-a1pyrimidin-6-yl)phenol; A mixture of 3-(dimethylamino)-2-(4-hydroxyphenyl)acrylaldehyde (5.00 g, 0.026 mol), 3-amino-4- bromopyrazole (4.23 g, 0.026 mol), 84 mL of ethanol and 4.2 mL of acetic acid was refluxed for 12 h. The mixture was cooled and the precipitate filtered off, washed twice with water and a small amount of ethanol, then dried in vacuum at 40-500C for 8 h. to give the desired phenol. Yield: 4.66 g (61.5%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; MERCK & CO., INC.; WO2007/85873; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1082745-50-3,Some common heterocyclic compound, 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, molecular formula is C9H14N4O2, 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 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (1.0 g, 4.76 mmol) and triethyl orthoformate (7.72 g, 47.6 mmol) in DMSO (20 mL) was added Cs2CO3 (3.1 g 9.5 mmol). The mixture was stirred at 130 C. for 36 hours. The mixture was diluted with water (100 mL) and extracted with DCM (30 mL*3). The organic layer was washed with water (30 mL*2) and dried over Na2SO4. The organic layer was evaporated under vacuum. The mixture was purified by silica gel chromatography (DCM: MeOH from 20:1 to 5:1) to give 6-methyl-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (560 mg, 50% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Marigo, Mauro; Kehler, Jan; Rasmussen, Lars Kyhn; (27 pag.)US2017/291901; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 345637-71-0,Some common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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.

Oxalylchloride (0.32 g, 2.6 mmol) and then one drop of N,Ndimethylformamidewere consecutively added to a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (0.45 g, 2.1 mmol) in 8 ml ofdichloromethane. The resulting mixture was stirred for 16 h at room temperatureand evaporated under reduced pressure. The residue was dissolved in 5 ml ofdichloromethane and added to a solution of ethyl 2-[2-(methylamino)ethyl]thiazole-4-carboxylate (23b, 0.65 g, 2.6 mmol) andtriethylamine (1.0 g, 10 mmol) in 5 ml of dichloromethane. The reaction mixturewas stirred for 4 h at room temperature, then diluted with water and extractedwith dichloromethane. The organic layer was washed with water and brine,dried over sodium sulfate and evaporated under reduced pressure, the remainderwas purified by chromatography on silica gel, using ethyl acetate / cyclohexane1 : 1 as eluent system to obtain ethyl 2-[2-[methyl-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]amino]ethyl] thiazole-4-carboxylate (24b,0.39 g, 1.0 mmol, 44 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, its application will become more common.

Reference:
Article; Sulzer-Mosse, Sarah; Lamberth, Clemens; Kubizna, Peter; Synlett; vol. 28; 17; (2017); p. 2277 – 2280;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic 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. Application In Synthesis of 4-Nitro-1H-pyrazole-3-carboxylic acid

15A. Synthesis of 5,6-dimethoxy-2-(4-m’tro-lH-pwazol-3-ylVlH-benzimidazoleTo a solution of EDC (4.81 g 25 mmol), HOBt (3.40 g, 25 mmol) and triethylamine (4.67 g, 46 mmol) in DMF (100 ml) was added 4-nitro-lH-pyrazole-3-carboxylic acid (3.63 g, 23.09 mmol) and 4,5-dimethoxy-benzene-l,2-diamine dihydrochloride (5.06g, 20.99 mmol) and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the resulting solid partitioned between EtOAc (50 ml) and saturated aqueous NaHCO3 (50 ml). A precipitate was formed and removed by filtration. The filtrate was washed with water followed by diethyl ether and then azeotroped with MeOH and toluene to yield 4- nitro-lH-pyrazole-3- carboxylic acid (2-amino-4,5-dimethoxy-phenyl)- amide (2.35 g, 36percent). 4-Nitro-lH-pyrazole- 3-carboxylic acid (2-amino-4,5-dimethoxy-phenyl)-amide (2.35g, 7.65 mmol) was dissolved in acetic acid (150 ml) and refluxed at 140° C for 5 hours. The solution was left to cool and the solvent removed in vacuo. The resulting solid was partitioned between EtOAc (25 ml) and brine (25 ml). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to yield 5,6-dimethoxy-2-(4-nitro-lH-pyrazol-3-yl)-lH-benzimidazol (2.08 ft 94percent).

The synthetic route of 4-Nitro-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2007/77435; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics