Day: August 11, 2021

Reference of 39806-90-1, 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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70C. The mixture was degassed for 2 hour at reduced pressure at 60-70C, cooled the mixture to 20-30C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63%);

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, 4-Iodo-1-methyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RALLIS INDIA LIMITED; PALIMKAR, Sanjay Sambhajirao; PAWAR, Jivan Dhanraj; SANKAR, B; KADAM, Subhash Rajaram; HINDUPUR, Rama Mohan; PRABHU, Venkatesh M.; PATI, Hari Narayan; SUPHALA, Vadiraj Gopinath; MANE, Avinash Sheshrao; WO2014/2109; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1572-10-7, These common heterocyclic compound, 1572-10-7, name is 3-Amino-5-phenylpyrazole, 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: The general method was described for the synthesis of D1. Compound C1 (150 mg, 0.393 mmol) was dissolved in ethanol (2 mL),followed by addition of 5-phenyl-1H-pyrazol-3-amine (62.63 mg, 0.393 mmol) and triethylamine (119.43 mg, 1.18 mmol). The mixture was stirred at room temperature for 5 h. The resultant mixture was purified by column chromatography to give D1.

The synthetic route of 1572-10-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuai; Shen, Dandan; Zhao, Lijie; Yuan, Xiaohan; Cheng, Jialing; Yu, Bin; Zheng, Yichao; Liu, Hongmin; Chinese Chemical Letters; vol. 31; 2; (2020); p. 418 – 422;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3994-50-1, name is 1-Methyl-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 3994-50-1, name: 1-Methyl-4-nitro-1H-pyrazole

General procedure: To a 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

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; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 35344-95-7, A common heterocyclic compound, 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, molecular formula is C4H4N2O, 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 li/-pyrazole-4-carbaldehyde (300 mg, 3.12 mmol) was added ethyl 2-(triphenylphosphoranylidene)acetate (1360 mg, 3.90 mmol) in toluene (10 mL). The mixture was heated at 90 °C for 2 h. The solvent was removed in vacuo. The crude material was purified by flash chromatography to afford Example 7A (450 mg, 2.71 mmol, 87percent yield) as a white solid. LCMS (ES): m/z 167.1 [M+H]+.

The synthetic route of 35344-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHAO, Guohua; DEVASTHALE, Pratik; YE, Xiang-Yang; SELVAKUMAR, Kumaravel; DHANUSU, Suresh; BALASUBRAMANIAN, Palanikumar; GUERNON, Leatte R.; CIVIELLO, Rita; HAN, Xiaojun; PARKER, Michael F.; JACUTIN-PORTE, Swanee E.; (290 pag.)WO2018/89353; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

2. Methyl 1 /-/-pyrazole-4-carboxylate was reacted with cyclopropylboronic acid and copper(ll) acetate to generate methyl 1 -cyclopropyl-1 /-/-pyrazole-4-carboxylate, which was hydrolyzed with lithium hydroxide to afford 1 -cyclopropyl-1 /-/-pyrazole-4- carboxylic acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 7119-95-1, These common heterocyclic compound, 7119-95-1, name is 1-Nitropyrazole, 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.

Step A: A stirred mixture of 1-nitropyrazole (3.45 g, 30.5 mmol) in benzonitrile (33 mL) was heated at 180 C. for 3 h. The mixture was cooled to rt, diluted with hexane and stirred at rt for 20 min. The precipitated solid was collected by filtration to afford 3-nitro-1H-pyrazole as a tan solid (3.16 g, 91%). 1H NMR (300 MHz, DMSO-d6) delta 13.94 (br s, 1H), 8.03 (d, J=2.4 Hz, 1H), 7.03 (t, J=2.4 Hz, 1H).

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1613191-73-3, 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. 1613191-73-3, name is Allyl 3,5-diamino-1H-pyrazole-4-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of allyl 3,5-diamino-lH-pyrazole-4-carboxylate 3 (1 g, 5.489 mmol) in DMF (5 mL) was added (Z)-2-chloro-3-dimethylamino-prop-2-enylidene]- dimethyl-ammonium hexafluorophosphate (1.683 g, 5.489 mmol), followed by triethylamine (722.1 mg, 994.6 mu, 7.136 mmol). The reaction mixture was heated to 60C for 4h during which time a solid slowly precipitated out of solution. The brown suspension was allowed to cool down to RT. The solid was filtered, washed with water and dried under vacuum to give allyl 2-amino-6-chloro-pyrazolo[l,5-a]pyrimidine-3-carboxylate 4b as a brown solid (1.092 g, 72% yield).

The synthetic route of Allyl 3,5-diamino-1H-pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; AHMAD, Nadia; BOYALL, Dean; CHARRIER, Jean-Damien; DAVIS, Chris; DAVIS, Rebecca; DURRANT, Steven; ETXEBARRIA I JARDI, Gorka; FRAYSSE, Damien; JIMENEZ, Juan-Miguel; KAY, David; KNEGTEL, Ronald; MIDDLETON, Donald; ODONNELL, Michael; PANESAR, Maninder; PIERARD, Francoise; PINDER, Joanne; SHAW, David; STORCK, Pierre-Henri; STUDLEY, John; TWIN, Heather; WO2014/89379; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 2075-45-8, The chemical industry reduces the impact on the environment during synthesis 2075-45-8, name is 4-Bromo-1H-pyrazole, I believe this compound will play a more active role in future production and life.

4-Bromo-1-ethyl-1H-pyrazole_: To a suspension of NaH (0.196 g, 8.16 mmol) in THF (15 ml_) was added 4-bromo- 1 H-pyrazole (1 g, 6.80 mmol) in THF (5 ml_) at 0 C, under nitrogen atmosphere, and strirred for 20 min. Ethyl iodide (0.825 ml_, 10.21 mmol) was added at 0 C and stirred at RT for 2 h. The reaction mixture was quenched with cold water, and extracted with EtOAc (2X). The organic layer washed with brine, dried under anhydrous Na2S04and filtered. The filtrate was concentrated and was purified by column chromatography to afford 4- bromo-1-ethyl-1 H-pyrazole (900 mg, 5.12 mmol, 75 % yield). LC-MS m/z 174 (M+H)+, 1.84 min (ret. time).

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, 4-Bromo-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1029413-51-1,Some common heterocyclic compound, 1029413-51-1, name is 4-Amino-1-(1-boc-azetidin-3-yl)-1H-pyrazole, molecular formula is C11H18N4O2, 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 14: Synthesis of I -(2-(2-(2-((I -(azetidin-3-yl)-I H-pyrazol-4-yl)amino)-5- chloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide (14)H2N.O H2NO_ H1BoC_NN/j NH2 + CI N1>A14 A18HNNNY(a) tert-Butyl 3-(4-((4-(2-(1-carbamoylcyclopropyl)phenethyl) -5-chloropyrimidin-2-yI)amino)- 1H-pyrazol- 1-yI)azetidine- 1-carboxylate (A 18) A suspension of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.100 g, 0.297 mmol), 052003 (0.291 g, 0.892 mmol) and tert-butyl 3-(4-amino-1H-pyrazol-1-yl)azetidine-1-carboxylate (0.142 g, 0.595 mmol) in dioxane (3 mL) was sonicated for 10 minutes. Xantphos(6.9 mg, 12 pmol) and Pd(ll) acetate (1.3 mg, 5.9 pmol) were added to thesuspension and the mixture was irradiated in the microwave for 20 minutes at 120 00 The resulting mixture was adsorbed onto silica gel and purified by columnchromatography (Biotage Isolera, 24 g Si02 cartridge, 0-100% EtOAc in petroleum benzine 40-60 00 then 0-40% MeOH in EtOAc) to give the title compound A18 as ayellow oil (110 mg, 69%). LCMS-A: rt 6.349 mm; m/z 538.3 [M+H].

The synthetic route of 1029413-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 15366-34-4, These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-carboxylate, 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 50 mL flask was charged with 1.89 g of startingmaterial 1 (15mmol), 1.96 g of starting material 2 (10 mmol),400 mg of Cul (2.0 mmol), 4.5 gofK 2C 0 3 (3.3 mmol) and 0.9mL of trans-N,N’-dimethylcyclohexayldiamine (2.0 mmol).The resulting mixture was stirred at 140 C. for 3 h. After themixture was cooled down to room temperature, 200 mL ofEtOAc was added and the oiganics were washed with water(2×50 mL), brine (2×50 mL). The oiganics were dried overM gS04 and concentrated under reduced pressure. The residuewas purified via flash chromatography on silica gel(0-25% EtOAc in hexanes) to get the desired product 3 (1.2 g,50%).

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ChemoCentryx, Inc.; Fan, Junfa; Krasinski, Antoni; Lange, Christopher W.; Lui, Rebecca M.; McMahon, Jeffrey P.; Powers, Jay P.; Zeng, Yibin; Zhang, Penglie; US2014/154179; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics