Tag: M.W=0-100

Reference of 288-13-1, 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. 288-13-1, name is 1H-Pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-isopropyl-1H-pyrazole : To a solution of pyrazole (50.0 g, 735.3 mmol) in aqueous sodium hydroxide (123.5 g NaOH/200 ml of water), was added isopropyl bromide (180.0 g, 1470.1 mmol) and the mixture was then heated to reflux for 6-7 days. The reaction mixture was cooled and extracted with ethyl acetate (3 x 300 ml). The combined organic layers were dried over MgS0₄₆) delta: 7.72 (d, J= 2.3 Hz, 1H), 7.41 (t, 1H), 6.21 (t, 1H), 4.5 (q, 1H), 1.41-1.37 (d, J= 11.1 Hz).

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

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2005/12254; (2005); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 28491-52-3,Some common heterocyclic compound, 28491-52-3, name is 5-Amino-1H-pyrazol-3(2H)-one, molecular formula is C3H5N3O, 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.

5-Amino-2,3-dihydro-1 H-pyrazol-3-one is dissolved in aqueous EtOH containing KOH. To this solution is added methyl 3-(3-trifluoromethyl-phenyl)-3-oxopropanoate and the mixture is stirred under reflux for 1 h 30 min. After cooling to rt, water is added and the mixture is acidified by addition of acetic acid to pH~5. The resulting precipitate is collected on a filter, washed with water and diethyl ether, and dried to give the title compound in moderate yield. Mp >;250 0C (decomp.); 1H-NMR (200 MHz, DMSO-d6), delta (ppm) 5.46 (s, 1 H); 6.05 (s, 1 H); 7.75 (t, 4 Hz, 1 H); 7.89 (d, 4 Hz, 2H); 8.07-8.12 (m, 1 H); 10.90 (br s, 1 H) and 12.25 (br s, 1 H). LC-MS m/z 296 (M+1 )

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-1H-pyrazol-3(2H)-one, its application will become more common.

Reference:
Patent; MERZ PHARMA GMBH &; CO. KGAA; HENRICH, Markus; BAUER, Angela; KRUeGER, Bjoern; KAUSS, Valerjans; MUeLLER, Sibylle; KUBAS, Holger; ROZHKOVS, Jevgenijs; PISKUNOVA, Irene; WO2010/139483; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1904-31-0, These common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, 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.

Example 149:; 4-(4-Dimethylcarbamoyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1 -methyl-1 H-pyrazol-3-yl)-amide; To a solution of 4-(4-dimethylcarbamoyl-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofurapi-6-carboxylic acid (149c) (130 mg, 0.366 mmol), 3-amino-1-methyl-pyrazole (71.1 mg, 0.732 mmol) and triethylamine (0.102 ml, 0.732 mmol) in 3 mL of DMF was added HATU (278 mg, 0.732 mmol). The mixture was stirred at 500C for 2 hr, quenched with water, extracted with 3XEtOAc. The combined organic layer was washed with 2XH2O, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 75- 100percent EtOAc in hexanes to give a white solid (134 mg, 84percent yield). 1H NMR (400 MHz, CDCI3) delta 8.69 (s, 1 H) 7.38 – 7.46 (m, 2 H) 7.24 – 7.28 (m, 1 H) 7.01 (d, J=2.78 Hz, 2 H) 6.97 (d, ./=8.59 Hz, 2 H) 6.77 (d, J=2.02 Hz, 1 H) 3.76 (d, 3 H) 3.07 (d, J=22.48 Hz, 6 H) 2.89 (s, 2 H) 1.47 (s, 6 H); LCMS for C24H26N4O4 m/z 435.20 (M+H+); Anal. Calcd. for C24H28N4O4- 0.7 H2O: C, 64.47; H, 6.18; N, 12.53; Found: C, 64.22; H, 6.11; N, 12.54.

Statistics shows that 1-Methyl-1H-pyrazol-3-amine is playing an increasingly important role. we look forward to future research findings about 1904-31-0.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2007/122482; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 28466-26-4, 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 28466-26-4 as follows.

To a solution of 1H-pyrazol-4-amine (300 mg, 95% purity, 3.43 mmol) in acetonitrile(17 mL) were added 2,2-difluoroethyl trifluoromethanesulfonate (690 p1, 5.1 mmol, CASRN 74427-22-8), powdered potassium carbonate (1 .06 g, 7.65 mmol), and triethylamine (720 pL, 5.1 mmol). The mixture was heated to 12000 overnight. For work-up, it was filtered, and the solid was rinsed with ethyl acetate. Concentraction of the filtrate in vacuo followed by flash chromatography led to the title compound (505 mg, 90% yield, 90%purity).LC-MS (Method B): Rt = 0.43 mm MS (ESIpos): mlz = 148 (M–H)1HNMR (400MHz, DMSO-d6) oe [ppm]: 3.23 (tdd, 2H), 4.72 (t, 1H), 6.05 (tt, 1H), 7.12 (s,2H), 12.10 (s, 1H).

According to the analysis of related databases, 28466-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 31108-57-3, The chemical industry reduces the impact on the environment during synthesis 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of crude reactant (122.6 mg, 0.287 mmol, theoretical amount) in anhydrous THF (3 mL) was added 4-cyanopyrazole (134 mg, 1.435 mmol) followed by potassium carbonate (198 mg, 1.435 mmol). The solution was heated at 60 C overnight. Then the solution was diluted with ethyl acetate (200 mL). The resulting solution was washed with brine (2×100 mL), dried overmagnesium sulfate and concentrated in vacuo. The crude product was purified by reverse phase prep-HPLC to afford desired product SB-5 (12.4 mg, 0.0282 mmol, two steps overall yield=9.8%) and by-product (4.2 mg, 0.00955 mmol, two steps overall yield=3.3%) as white solid. Compound SB-5 1HNMR (400 MHz, CDC13) 5(ppm): 7.86 (s, IH), 7.81 (s, IH), 5.02 (AB, IH), 4.90 (AB, IH), 3.42 (AB, IH), 3.40 (S, 3H), 3.39 (AB, IH), 2.64 (s, IH), 2.61 (t, IH), 1.00-2.25 (m, 23H), 0.67 (s, 3H). LC-MS: rt = 2.32 mm, m/z =440.2 [M+H]+

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, 1H-Pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, 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 930-36-9, COA of Formula: C4H6N2

To a mixture of 1-methyl-1H-pyrazole (16.4 g, 0.2 mol, 1.0 eq) in dry THF (150 mL) was added n-BuLi (2.5 M in hexane, 96 mL, 0.24 mol, 1.2 eq) at -78 C. under nitrogen atmosphere. The mixture was stirred at -78 C. for 1 h. Then DMF (30.8 mL, 0.4 mol, 2.0 eq) was added dropwise and the mixture was stirred for 1 h. TLC analysis of the reaction mixture showed full conversion to the desired product. The reaction was quenched with a saturated aqueous solution of NH4Cl and extracted with EA (3×500 mL). The organic layer was washed with brine and water, dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on a silica gel to give compound OI-5a (12.7 g, 58%).

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-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Foresee Pharmaceuticals Co., Ltd.; YANG, Wenjin; CHANG, Kai-Wei; LIU, Suying; TSAI, Cheng-Han; (98 pag.)US2019/352288; (2019); 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. 930-36-9, name is 1-Methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Methylpyrazole

To a solution of 1 -methyl pyrazole (4.1 g, 50 mmole) in THF (100 mL) at 00C was added n-BuLi (2.2M in THF, 55 mmole). The reaction solution was stirred for 1 hour at RT and then cooled to -78C [J. Heterocyclic Chem. 41 , 931 (2004)]. To the reaction solution was added 2-isopropoxy-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (12.3 mL, 60 mmole). After 15 min at -78C, the reaction was allowed to warm to 00C over 1 hour. The reaction was diluted with saturated NH4CI solution and extracted with DCM. The organics were dried over Na2SO4 and concentrated under vacuum to afford a tan solid (8.0 g, 76%) which was used without further purification. LCMS (ES) m/z 127 (M+H)+ for [RB(OH)2]; 1H NMR (CDCI3, 400 MHz) delta 7.57 (s, 1 H), 6.75 (s, 1 H), 4.16 (s, 3H), and 1.41 (s, 12H).

The synthetic route of 930-36-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/98105; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 3920-50-1, These common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, 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.

EXAMPLE 3 Synthesis of 3-pyrazolecarbaldehyde-(5-nitro-2-pyridyl)hydrazone (compound 3) A desired product was obtained in the same manner as in Example 1 by using 3.20 g (20.8 mmol) of 5-nitro-2-pyridylhydrazine and 1.90 g (19.8 mmol) of 3-pyrazolecarbaldehyde. Yield: 3.92 g (16.9 mmol) [yield rate: 85percent] Melting point: 286° to 287° C.

The synthetic route of 3920-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kabushiki Kaisha Toshiba; US5569763; (1996); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 36650-74-5, The chemical industry reduces the impact on the environment during synthesis 36650-74-5, name is 1H-Pyrazole-3-carbonitrile, I believe this compound will play a more active role in future production and life.

To a solution of II-D12 (165 mg, 0.4 mmol) in acetone (5 mL) was added K2C03 (96.9 mg, 0.7 mmol) and lH-pyrazole-4-carbonitrile (65.4 mg, 0.7 mmol) at l5C. The reaction mixture was stirred for 16 hours at l5C. The reaction mixture was added into saturated NH4Cl (20 mL). The aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with saturated brine (50 mL), dried over anhydrous Na2S04, filtered and concentrated to give product. The residue was purified by combi flash (0-20% of EtOAc in PE) to give II-D13 (74.6 mg, 44.1%) as a solid. (1069) 1H NMR (400 MHz, CDCl3) dH 7.47 (d, J= 2.4 Hz, 1H), 6.72 (d, J= 2.4 Hz, 1H), 4.96 (dd, J = 17.6, 51.2 Hz, 2H), 3.52 (q, J = 6.8 Hz, 2H), 3.21 (s, 2H), 2.59 (t, J = 8.8, 1H), 2.25-2.10 (m, 2H), 1.90-1.60 (m, 6H), 1.55-1.10 (m, 18H), 1.05-0.80 (m, 5H), 0.68 (s, 3H); MS ESI calcd. for C29H42N302 [M-H20+H]+ 464, found 464.

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, 1H-Pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAGE THERAPEUTICS, INC.; ROBICHAUD, Albert, Jean; SALITURO, Francesco, G.; BLANCO-PILLADO, Maria, Jesus; LA, Daniel; HARRISON, Boyd, L.; (276 pag.)WO2019/126741; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-13-1, name is 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. Quality Control of 1H-Pyrazole

4-Nitropyrazole is available commercially from the N.D. Zelinsky Institute, Organic Chemistry, Leninsky prospect 47, 117913 Moscow B-334, Russia. The compound may also be prepared as follows :-; Fuming nitric acid (9.5 ml) was added drop wise to a stirred solution of pyrazole (13.6 g) in glacial acetic acid (51 ml) that had been cooled to -10°C using an ice-salt bath. A voluminous precipitate was formed. Acetic anhydride (27 ml) was added dropwise and the resultant mixture was stirred at ambient temperature for 2.5 hours. The mixture was poured onto ice and the acidity of the mixture was reduced to peta5 by the addition of potassium carbonate. The precipitate was isolated by filtration. The resultant solid was dissolved in water and the aqueous solution was extracted with diethyl ether. The organic solution was dried over magnesium sulphate and filtered. Petroleum ether (b.p. 60-800C, 50 ml) was added to the filtrate which was concentrated by evaporation to a volume of about 50 ml. A precipitate formed which was isolated by filtration. This solid was believed to be 1-nitropyi-azole (20.6 g); 1H NMR Spectrum: (DMSOd6) 6.71 (s, IH), 7.88 (s, IH), 8.81 (s, IH). The compound may be explosive and should be handled cautiously.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/113565; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics