Category: pyrazoles-derivatives

Adding a certain compound to certain chemical reactions, such as: 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-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 181585-93-3, SDS of cas: 181585-93-3

Methyl 3-nitro-1H-pyrazole-5-carboxylate (1.71 g,10 mM) was dissolved in methanol (40 mL), and 10% Pd/C (0.26 g) was added. Hydrogenation wascarried out in a Paar apparatus under 5 bar. After 24 h, the catalyst was filtered o and washedby methanol. The solvent was evaporated by reduced pressure, and the residue was crystallizedfrom ethanol (10 mL). Yield: 1.14 g, 81%. Melting point by DSC: 116 and 142 C (Figure S23). TLC:CHCl3/MeOH/AcOH (90:8:2) Rf = 0.43. Elemental analysis for C5H7N3O2: calculated C, 42.55%; H,4.96%; N, 29.79%; found: C, 42.70%; H, 5.00%; N, 29.71%. 1H NMR (400MHz, DMSO-d6) delta(ppm):tautomer T5; 12.16 (1H, s, N-HPz), 5.68 (1H, s, C-HPz), 5.19 (2H, s, NH2), 3.75 (3H, s, CH3), tautomerT3; 12.60 (1H, s, N-HPz), 5.92 (1H, s, C-HPz), 4.81 (2H, s, NH2), 3.75 (3H, s, CH3) (Figure S15). 13CNMR (400 MHz, DMSO-d6)delta (ppm): tautomer T5; 159.65 (C=O), 148.85 (C-NH2), 132.54 (C-C=O),89.04 (C4-H), tautomer T3; 162.87 (C=O), 156.20 (C-NH2), 142.35 (C-C=O), 94.27 (C4-H).

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Reference:
Article; Kusakiewicz-Dawid, Anna; Porada, Monika; Dziuk, B?azej; Siod?ak, Dawid; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
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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. 180207-57-2, name is 2-(1H-Pyrazol-4-yl)ethanol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

EXAMPLE 11; Preparation of 2-(4-(2-Chlorophenyl)-2-{4-[2-(1H-pyrazol-4-yl)ethoxy]phenyl}-thien-3-yl)-N-(diaminomethylene)acetamide; To a solution of methyl [4-(2-chlorophenyl)-2-(4-hydroxyphenyl)thien-3-yl]acetate (0.485 g, 1.35 mmol), 2-(1H-pyrazol-4-yl)-ethanol (0.166 g, 1.48 mmol), and PPh3 (0.388 g, 1.4 mmol) in THF (3 mL) was added at 0 C. diethyl azo-dicarboxylate (DEAD) (0.265 g, 0.24 mL, 1.52 mmol). The solution was stirred overnight and the solvent removed. The product was purified directly by flash chromatography (20:1 CHCl3:MeOH) to yield methyl (4-(2-chlorophenyl)-2-{4-[2-(1H-pyrazol-4-yl)ethoxy]phenyl}thien-3-yl)acetate (0.565 g). This material was reacted as in Example 1, Steps 7 and 8 to yield 2-(4-(2-chlorophenyl)-2-{4-[2-(1H-pyrazol-4-yl)ethoxy]phenyl}thien-3-yl)-N-(diaminomethylene)acetamide (0.151 g) as a white solid. mp 71-72 C.; 1H NMR (500 MHz, DMSO-d6) delta: 2.90 (t, 2H, J=6.7 Hz), 3.50 (s, 2H), 4.15 (t, 2H, J=6.9 Hz), 7.05 (m, 2H), 7.44 (m, 6H), 7.55 (m, 2H), 7.70 (s, 1H). MS (ES) m/z 478.1 ([M-H]-). MS (ES) m/z 538.1 ([M+CH3COO]-). MS (ES) m/z 957.3 ([2M-H]-). Anal. Calcd for C24H22ClN5O2S.H2O: C, 57.88; H, 4.86; N, 14.06. Found: C, 55.49; H, 5.37; N, 14.80. A description of 2-(1H-pyrazol-4-yl)-ethanol can be found in Jones and Mann, J. Am. Chem. Soc., 75, 4048-52; 1953.

The synthetic route of 180207-57-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US2006/183792; (2006); 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;,
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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 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;,
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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;,
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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

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

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

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