Tag: M.W:200-300

Reference of 39806-90-1, These common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-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.

To a solution of 4-iodo-1-methyl-1H-pyrazole (3.0 g, 14.4 mmol, 1.0 eq.), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) (835 mg, 1.4 mmol, 0.1 eq.) and palladium(II) acetate (415 mg, 0.7 mmol, 0.05 eq.) in dioxane (72.1 ml, 0.2 M) was added N,N’-diisopropylethylamine (5.0 mL, 28.9 mmol, 2.0 eq.) and benzylmercaptan (2.0 ml, 17.3 mmol, 1.2 eq.). The reaction mixture was stirred at 100 C for 18 h. The reaction mixture was diluted with ethyl acetate (300 mL) and water (150 mL). The aqueous layer was extracted with ethyl acetate (150 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by column chromatography.

The synthetic route of 39806-90-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Vernier, William F.; Gomez, Laurent; Tetrahedron Letters; vol. 58; 49; (2017); p. 4587 – 4590;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13599-12-7, name is Ethyl 3-phenyl-1H-pyrazole-5-carboxylate, 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 13599-12-7, category: pyrazoles-derivatives

General procedure: A mixture of ethyl 3-aryl-1H-pyrazole-5-carboxylate 1 (2 mmol), N-aralkyl -2-chloroacetamide 7 (3 mmol), anhydrous potassium carbonate (4 mmol) and dry acetonitrile (60 ml) was refluxed for 1-5 h, after which the mixture was cooled to room temperature and filtered. The filtrate was condensed under reduced pressure. The crude product was purified by chromatographer on silica gel using PE/EtOAc (3:1) as an eluent to afford the desired compounds 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:
Article; Lv, Hong-Shui; Kong, Xiang-Qian; Ming, Qian-Qian; Jin, Xing; Miao, Jun-Ying; Zhao, Bao-Xiang; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 844 – 849;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-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 1-Benzyl-4-iodo-1H-pyrazole

General procedure: A mixture of K2CO3 (0.552 g, 4.0 mmol), Ph3P (5.3 mg,0.02 mmol) and 10% palladium on charcoal (10.6 mg, 0.01 mmol) in EtOH(10 ml) was stirred gently for 30 min, then the hetaryl halide (1.0 mmol) andterminal acetylene (1.2 mmol) were added. The mixture was stirred gently atreflux for 48 h. The resulting precipitate was filtered through a pad of silica geland the EtOH was evaporated. Pure product was isolated by columnchromatography on silica gel using petroleum ether/EtOAc as eluent

The synthetic route of 1-Benzyl-4-iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arsenyan, Pavel; Rubina, Kira; Vasiljeva, Jelena; Belyakov, Sergey; Tetrahedron Letters; vol. 54; 48; (2013); p. 6524 – 6528;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 866837-96-9,Some common heterocyclic compound, 866837-96-9, name is Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, molecular formula is C12H13N3O2, 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.

1 -Phenyl-5-(pyridin-2-ylamino)-1 H-pyrazole-3-carboxylic acid; 200mg (0,865 mmol) of 5-Amino-1 -phenyl-1 H-pyrazole-3-carboxylic acid ethyl ester were dissolved in 5 ml DMF and 108mg (0,95 mmol, 1 .1 eq) of 2-Chloropyridine, 620mg (1 ,9mmol, 2,2eq) of Cs2C03, 20mg (0, 1 eq) of palladium(ll)acetate and 60mg of xantphos (0, 12eq) were added and the resulting mixture heated to 100C for 6 hours. The mixture was filtered over a pad of Celite and 2 ml of 1 N NaOH (2mmol, 2,3eq) were added together with 2ml of EtOH. After stirring overnight at RT the crude reaction mixture was subjected to HPLC chromatography delivering 60mg of product. (Yield: 25%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; SANOFI; RUF, Sven; SADOWSKI, Thorsten; HORSTICK, Georg; SCHREUDER, Herman; BUNING, Christian; OLPP, Thomas; WIRTH, Klaus; WO2012/101199; (2012); 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. 84547-84-2, name is 4-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H5BrN2O2

A mixture of 4-bromo-l-methyl-lH-pyrazole-5-carboxylic acid (5.0 g, 24.4 mmol) and BH3.THF (36.6 mL of a 1 M solution in THF, 36.6 mmol) in THF (50 mL) was stirred at 50 C for 2 days; at this point LCMS showed the completion of the reaction. The reaction was cooled to RT and cautiously quenched with aq. 1N F1C1 and stirred at RT for 1 h, after which the mixture was extracted with EtOAc (3 X 50 mL). The combined organic extracts were concentrated in vacuo. The residue was (0667) chromatographed (80 g S1O2; continuous gradient from 0% to 100% EtOAc in hexanes, 25 min) to give the title compound (3.60 g, 18.9 mmol, 77 % yield) as a white solid. LCMS, [M+H]+ = 193.0.

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 84547-84-2.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SHI, Yan; CHENG, Peter Tai Wah; ZHANG, Hao; LI, Jun; FANG, Tianan; CORTE, James R.; (135 pag.)WO2019/126103; (2019); 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. 1105039-93-7, name is 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-(4-Methoxybenzyl)-1H-pyrazole-4-carboxylic acid

To resin PL-TFP, 1 .4mmol/g, 150-300um (300 mg) was added a solution of 1 -(4- methoxybenzyl)-1 H-pyrazole-4-carboxylic acid (64 mg, 0.276 mmol) and 4-DMAP (20 mg, 0.164 mmol) in DCM (4 ml)/DMF (1 ml). After 10 min shaking at rt, Nu,Nu’- diisopropylcarbodiimide (0.172 ml, 1 .102 mmol) was added and the mixture was shaked at rt overnight. The resin (loaded with the activated ester) was filtered and washed with DMF (2ml), DCM (10 ml) and THF (10 ml). The wet resin was suspended in THF (3ml), then pipetted back to flask. A solution of the amine 5-chloro-1 H-indazol-3- yl)methanamine (50 mg, 0.275 mmol) and TEA (230 muIota_, 1 .653 mmol) in THF (2 ml) was added to the resin suspension and the mixture was shaked at rt for 4 days, filtered and washed with THF. The filtrate was diluted with EtOAc and washed with HCI 1 N, aq. sat. NaHC03 and brine. The organic layer was dried (Na2S04), filtered and concentrated. The residue was triturated with ACN (1 ml), the precipitate was filtered, washed with ACN (1 ml) and dried on HV.UPLC RtE= 0.85 min, [M+H]+ = 396.3-398.4, 1H NMR (400 MHz, DMSO-d6) delta ppm 3.71 (s, 3 H) 4.68 (d, 2 H) 5.23 (s, 2 H) 6.70 – 6.99 (m, 2 H) 7.10 – 7.26 (m, 2 H) 7.31 (dd, 1 H) 7.50 (d, 1 H) 7.81 – 7.93 (m, 2 H) 8.20 (s, 1 H) 8.65 (br. s., 1 H) 13.01 (s, 1 H).

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 1105039-93-7.

Reference:
Patent; NOVARTIS AG; FLOHR, Stefanie; MARKERT, Christian; NAMOTO, Kenji; PIRARD, Bernard; WO2013/111108; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 10250-64-3, The chemical industry reduces the impact on the environment during synthesis 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, I believe this compound will play a more active role in future production and life.

To a stirred suspension of l-methyl-3-phenyl-lH-pyrazole-5-carboxylic acid (46 mg, CAS 10250-64-3) in dichloro ethane (2 ml) were added oxalyl chloride (44 mu) and DMF (2 drops). The reaction mixture was stirred at room temperature for 1 h and was then concentrated in vacuo. The residue was dissolved in THF (1 ml) and the resulting solution was added drop wise to a stirred solution of (+)-(R)-2-(4-amino-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (50 mg, example lh) and triethylamine (118 mu) in THF (2 ml). The reaction mixture was stirred at room temperature for 2 h. The crude reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (Si02; gradient: 0 % to 50 % EtOAc in heptane) to give (R)-2-{3-fluoro-4-[(2-methyl-5-phenyl-2H-pyrazole-3-carbonyl)-amino]- phenyl}-morpholine-4-carboxylic acid tert-butyl ester (81 mg, quant.) as a white solid. MS (ISP): 503.1 ([M+Na]+), 481.3 ([M+H]+), 425.2 ([M+H-C4H8]+).

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-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GALLEY, Guido; NORCROSS, Roger; PFLIEGER, Philippe; WO2012/168265; (2012); 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. 155600-99-0, name is 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dibromo-1-methyl-4-nitro-1H-pyrazole

Nucleophilic aromatic substitution of the compound 2 with benzylamine in DMSO produces benzyl-(5-bromo-2-propyl-4-nitro-2H-pyrazol-3-yl)-amine 3.

The synthetic route of 155600-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dahlgren, Richard Marc; Laidig, William David; Lim, Mu-ill; Murphy, Bryan Patrick; Zhang, Guiru; US2009/282622; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1239363-40-6,Some common heterocyclic compound, 1239363-40-6, name is 1-Cyclopropyl-4-iodo-1H-pyrazole, molecular formula is C6H7IN2, 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 1-cyclopropyl-4-iodo-1H-pyrazole Intermediate 4a (500 mg, 2.13 mmol) in 1,4-dioxane (10 mL) was added benzyl mercaptan (527 mg, 4.30 mmol), NNdiisopropylethylamine (554 g, 4.30 mmol), tris(dibenzylideneacetone)dipalladium (20mg, 0.020 mmol) and 9,9-dimethyl-4, 5-bis(diphenylphosphino)xanthene (23 mg, 0.040 mmol) under nitrogen atmosphere. After stirred at 110 C overnight, the reaction mixture was cooled down to room temperature and diluted with water (20 mL), extracted with ethyl acetate (20 mL) for three times. The combined organic layers were washed with brine (20 mL), dried over Na2SO4() and filtered. The filtrate wasconcentrated under reduced pressure to give a crude product, which was purified by silica gel column chromatography (petroleum ether : ethyl acetate = 10 : 1) to to afford the title compound (330 mg, 67 % yield) as colorless oil. LC-MS (ESI): RT = 2.358 mm, mass calcd. for C13H14N2S 230.1, mlz found 230.9 [M+H]. ?HNIVII{ (300 1VIHz, CDC13)7.32-7.17 (m, 4H), 7.13 -7.07 (m, 3H), 3.78 (s, 2H), 3.57-3.46 (m, 1H), 1.07-0.92 (m, 4H).

The synthetic route of 1239363-40-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; WAN, Zhao-Kui; JIANG, Yimin; DAI, Xuedong; LIU, Qian; CHEUNG, Wing Shun; DENG, Gang; FU, Liqiang; (547 pag.)WO2019/1420; (2019); 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. 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 330792-70-6

Step 5. Preparation of tert-butyl 3-(5-amino-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate To a solution of tert-butyl 3-(tosyloxy)piperidine-1-carboxylate (355 mg, 1.0 mmol) and 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (276 mg, 1.0 mmol) in 5 mL of DMF is added Cs2CO3 (650 mg, 2.0 mmol). A tosyloxy leaving group is employed in this reaction. The mixture is stirred at RT for 16 hours, 75 C. for 3 hours and 60 C. for 16 hours. The mixture is concentrated washed with brine (100 mL*3) and dried over Na2SO4. The material is concentrated and purified by chromatography column on silica gel (eluted with petroleum ether/ethyl actate=3/1) to afford 60 mg (13%) of tert-butyl 3-(5-amino-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate as a yellow oil.

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 330792-70-6.

Reference:
Patent; Acerta Pharma B.V.; Lannutti, Brian; Rothbaum, Wayne; Barf, Tjeerd; Kaptein, Allard; (231 pag.)US2017/35881; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics