Day: August 23, 2021

Synthetic Route of 175137-46-9, These common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-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.

Intermediate 15 2,5-dichloro-N-(5-cvclopropyl-lH-pyrazol-3-yl)pyrimidin-4-amine [0096] A mixture of 5-cyclopropyl-lH-pyrazol-3-amine (246 mg, 2.00 mmol), 2,4,5-trichloropyrimidine (367 mg, 2.00 mmol, 1 equiv.) and Na2CO3 (233 mg, 2.20 mmol, 1.1 equiv.) in EtOH (10 mL) was heated at 40 0C for 16 h. The crude reaction mixture was diluted with EtOAc and sequentially washed with: water (3x) and saturated aqueous NaCl (Ix). The resulting EtOAc layer was dried over Na2SO4 and then concentrated in vacuo, providing 2,5-dichloro-N-(5-cyclopropyl-lH-pyrazol-3- yl)pyrimidin-4-amine; ESMS m/z 270.0 (M + H+).

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 3920-50-1,Some common heterocyclic compound, 3920-50-1, name is Pyrazole-3-carboxaldehyde, molecular formula is C4H4N2O, 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.

1.04 g (15 mmol) of hydroxylamine hydrochloride, 1.23 g (15 mmol) of sodium acetate and 40 ml of ethanol were added to a 100 ml three-necked flask, and 0.96 g (10 mmol) of 3-formalpyrazole was added thereto with stirring.The temperature was raised to 60 C and the reaction was carried out for 3 h. After the reaction, the milky white turbid liquid was obtained and cooled to room temperature.filter,The filtrate was evaporated to give an oily viscous solid, which was dissolved in 50 ml of water.Extract 50 times with 50 ml of ethyl acetate.The organic phase was dried over anhydrous sodium sulfate and filtered.The filtrate was evaporated to dryness to give a pale yellow viscous solid 0.99 g.The yield was 89.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Pyrazole-3-carboxaldehyde, its application will become more common.

Reference:
Patent; Xi’an Modern Chemical Institute; Zhang Yiying; Li Purui; Zhou Cheng; Wang Wei; Sun Chenghui; (7 pag.)CN109438353; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 881668-70-8,Some common heterocyclic compound, 881668-70-8, name is 5-Chloro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3ClN2O2, 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.

Method E A mixture of TBTU (642 mg, 2.0 mmol), pyrazole-3-carboxylic acid or 5-chloro pyrazole-3-carboxylic acid (intermediate II) (1.0 mmol), the relevant arylamine (1.0 mmol), DIPEA (348 muL, 2.0 mmol) and DMAP (12 mg, 0.1 mmol) in dry DMF (5 mL) was stirred at 80 0C for 3 days. After cooling to rt the mixture was concentrated and hydrochloric acid (IM, 10 mL) was added. The mixture was extracted with EtOAc (4 x 10 mL) , the combined organic phases washed with NaCl (sat., aq.; 20 mL), dried (Na2SO4), concentrated and purified by chromatography (EtO Ac/heptane) to give the desired compound.

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

Reference:
Patent; BIOLIPOX AB; WO2007/51981; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 112758-40-4, 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. 112758-40-4, name is 3-Methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 1-(2-(3-isobutyryl-1-methyl-1H-indol-5-ylamino)pyrimidin-4-yl)-3-methyl-1H-pyrazole-4-carbaldehyde; intermediate 6 To a solution of 3-methyl-1H-pyrazole-4-carbaldehyde (273 mg, 2.48 mmol) in anhydrous DMF (5 mL) was added 60% NaH (130 mg, 3.25 mmol) at 0 C. After being stirred for 30 min at room temperature, it was cooled to 0 C. To this, was added intermediate 5 (542 mg, 1.65 mmol) and then stirred for 6 hours at 60 C. Quenching the reaction by addition of ice and 20 mL of water resulted precipitation of brown solids. The resulted solids were collected by filtration, rinsed with water and the dried in vacuo to provide the desired intermediate 6 as a brown solid (424 mg, 80%); MS (ESI) m/z 403 [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, 3-Methyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lee, Jaekyoo; Choi, Jang-Sik; Hwang, Hae-Jun; Song, Ho-Juhn; Kim, Jung-Ho; Kim, Se-Won; Koh, Jong Sung; Lee, Jaesang; Lee, Tae-Im; Choi, Yung-Geun; Park, Sung-Ho; Lee, In Yong; Suh, Byung-Chul; Salgaonkar, Paresh Devidas; Jung, Dong-Sik; US2015/111883; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, 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 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde

To a solution of 4-(4-((1 ,2,4-oxadiazol-3-yl)methyl)piperazin-1 -yl)-5-chloro-3- nitropyridin-2-amine (50.0 mg, 0.147 mmol) and 1 ,3-dimethyl-1 /-/-pyrazole-4- carbaldehyde (19.2 mg, 0.155 mmol) in EtOH (3.4 mL) was added 1 M Na2S204 (0.588 mL, 0.588 mmol, freshly prepared) and the solution was heated to 80 C and stirred for 15 h whilst being open to air. Once cooled, the reaction was evaporated in vacuo and the residue dry loaded onto silica. Purification was accomplished by flash chromatography on silica gel (2 x 14) eluting with MeOH/CH2CI2 (5-7.5%) to yield the title compound (26 mg, 43%) as a pale yellow solid. [00129] 1 H-NMR (500 MHz, CDCI3) 2.58 (s, 3H, CH3), 2.81 (app t, J = 4.4 Hz, 4H, CH2), 3.82 (app s, 4H, CH2), 3.85 (s, 3H, NCH3), 3.88 (s, 2H, -CH2-), 7.62 (br s, 1 H, CHar), 7.87 (br s, 1 H, CHar), 8.74 (s, 1 H, CHar), 13.04 (s, 1 H, NH); [00130] LC – MS (ESI, m/z): Rt = 1 .91 min – 414, 416 [(M + H)+, CI isotopic pattern]; [00131] HRMS: Found: 436.1374, calculated for C18H20N9OCINa (M+Na)+: 436.1372.

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190319; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 35277-02-2, The chemical industry reduces the impact on the environment during synthesis 35277-02-2, name is 4-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(4-fluoro- lH-pyrazol- l-yl)propanamide (C14H10F4N4O) (0837) 1029 (0838) [00384] To a solution of 4-fluoro-pyrazole (0.20 g, 0.0023237 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.28 g, 0.0069711 mol). After addition, the resulting mixture was stirred for 3 h. 3- Bromo-N-(4-cyano-3-(trifluoromethyl)phenyl)propanamide (1029a, 0.75 g, 0.0023237 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at RT under argon. The reaction was quenched by water, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgS04, filtered, and concentrated under vacuum. The product was purified by a silica gel column using DCM and methanol (19: 1) as eluent to afford 0.75 mg (10%) of the titled compound as white solid. (0839) [00385] Compound 1029 was characterized as follows: NMR (400 MHz, DMSO-i delta 10.81 (s, 1H, NH), 8.25 (d, = 2.4 Hz, 1H, ArH), 8.10 (dd, = 8.8 Hz, = 2.4 Hz, 1H, ArH), 7.95 (d, = 8.8 Hz, 1H, ArH), 7.88 (s, 1H, Pyrazole-H), 7.46 (s, 1H, Pyrazole-H), 4.35 (t, J = 6.0 Hz, 2H, CH2), 2.79 (t, J = 6.0 Hz, 2H, CH2); Mass (ESI, Negative): 325.03 [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, 4-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (234 pag.)WO2017/214634; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 25016-20-0, name is 1-Methyl-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. Formula: C5H6N2O2

Boc protected macrocyclic amine Ac (65 mg, 0.081 mmol) is charged in a vial with a 4 M solution of HCI in dioxane (3 mL). The solution is stirred at RT for 1 h, after which the solution is evaporated to dryness. 1 -methyl- 1 H-pyrazole-3-carboxylic acid R2b (12.2 mg; 0.097 mmol, 1 .2 equiv) is dissolved in DMF (2 mL) and TEA (45.1 mu; 0.323 mmol, 4 equiv) and TBTU (29.9 mg; 0.097 mmol, 1 .2 equiv) are added. The mixture is stirred for 15 mins. The Boc de-protected macrocyclic amine hydrochloride Cc is dissolved in DMF (1 .0 mL) and added to the acid solution. The reaction is stirred at RT overnight. The resulting solution is filtered through a Millex filter and purified by prep HPLC (X-Bridge column, Ammonium Bicarbonate pH10: MeOH). The pure fractions are combined, concentrated, frozen and lyophilized to provide compound 1008.FIA M.S.(electrospray) : 812.3 (M+H)+ Retention time (min) = 6.8 min1H NMR (400 MHz,DMSO-d6): delta 10.83 (s, 1 H) , 8.91 (s, 1 H), 7.88- 7.77 (m, 2H), 7.75 (d, 1 H, J = 2.4 Hz), 7.36- 7.30 (m, 1 H), 6.62 (s, 1 H), 6.55 (d, 1 H, J = 2 Hz), 5.65- 5.57 (m, 1 H), 5.57- 5.45 (m, 2H), 5.15- 5.03 (m, 1 H), 4.64- 4.50 (m, 2H), 4.49- 4.37 (m, 1 H), 4.03- 3.88 (m, 1 H), 3.88 (s, 3H), 2.67-2.55 (m, 1 H), 2.38- 2.24 (m, 2H), 2.00- 1 .87 (m, 1 H), 1 .87-1 .72 (m, 1 H), 1 .61 – 1 .47 (m, 3H), 1 .47-1 .17 (m, 18H), 0.95- 0.78 (m, 2H).

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 26621-44-3, 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. 26621-44-3, name is 3-Nitro-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

To a 0 C. solution of 3-nitro-1H-pyrazole (250.0 g, 2.17 mol, 1.0 eq) in anhydrous DMF (2.5 L; 10.2 vol eq) under nitrogen was added NaH (95.42 g of 60% w/w, 2.39 mol, 1.1 eq) in batches over 30 min while maintaining temperature below 8 C. The mixture was stirred for 1 h then 2,4-difluoropyridine (300 mL, 3.29 mol, 1.5 eq) was added, and the reaction was warmed to room temperature and stirred for approximately 16 hours (h). The reaction mixture was diluted with water (12.5 L) and stirred vigorously for 1 h. The off-white solid was collected by vacuum filtration. The solid was re-suspended in water (2 L) and filtered, and this step was repeated once further. The product was dried under vacuum, then suspended in heptane (4 L), stirred 3 h at room temperature, and filtered. The solid was washed with two further portions of heptane (2 L each) and dried under vacuum to provide 2-fluoro-4-(3-nitro-1H-pyrazol-1-yl)pyridine (426.3 g of 92% purity, 87% yield). 1H NMR (400 MHz, DMSO-d6) delta 9.01 (d, J=2.8 Hz, 1H), 8.45 (d, J=5.7 Hz, 1H), 7.95 (ddd, J=5.7, 1.9, 1.2 Hz, 1H), 7.81 (t, J=1.4 Hz, 1H), 7.46 (d, J=2.8 Hz, 1H) ppm. ESI-MS m/z calc. 208.04, found 209.01 (M+1).

The chemical industry reduces the impact on the environment during synthesis 3-Nitro-1H-pyrazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Bligh, Cavan McKeon; Court, John J.; Liang, Jianglin; O’Dowd, Hardwin; Roeper, Stefanie; Ryan, Michael P.; US2019/177295; (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. 28466-26-4, name is 4-Aminopyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3

Imine (I1) A solution of 4-aminopyrazole (10) (10.5 g, 126 mmol), ethylacetoacetate (18.0 g, 140 mmol, 1.05 eq.) and a catalytic amount of para-toluenesulfonic acid monohydrate (1.3 g, 6.65 mmol, 5%) in 100 mL of benzene was refluxed with a Dean-Stark trap for about 1 hour. The end of reaction checked by TLC (Ethylacetate/Hexane 1/1, 4-aminopyrazole Rf=0.1, imine Rf=0.5, UV active, brown after overnight). Solvents were removed under vacuum and the imine was purified by running through a short silica chromatography column to give the desired product (11) as a tan solid (22.4 g, 125 mmol, 91%). GC/MS: m/z=195 (100%).

The synthetic route of 28466-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Neurocrine Biosciences, Inc.; US6531475; (2003); B1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 5071-61-4, name is 5-Phenyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Phenyl-1H-pyrazole-3-carboxylic acid

A solution of acid 4 (0.09 g, 0.47 mmol) in dry DMF (2 mL) treated sequentially with amine (5a-i, 6a-e and 7a-h; 0.517 mmol)and triethylamine (0.94 mmol) was stirred under a N2 atmosphere for 15 min, later TBTU (0.56 mmol) was added and reaction mixture refluxed for 4-10 h. The reaction mixture was quenched with aq satd NH4Cl solution (10 mL). After 10 min, it was diluted withCHCl3 (2 10 mL) and washed with water (10 mL), NaHCO3 solution(10 mL) and brine (10 mL). The organic layers were dried over anhydrous sodium sulfate, evaporated and the residue purified by column chromatography using 30% ethyl acetate in pet. ether to afford corresponding amides 8a-i, 9a-e and 10a-h.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Doma, Anuradha; Kulkarni, Ravindra; Palakodety, Radhakrishna; Sastry, G. Narahari; Sridhara, Janardhan; Garlapati, Achaiah; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 6209 – 6219;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics