Day: July 28, 2021

Synthetic Route of 3469-69-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3469-69-0 name is 4-Iodopyrazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-Iodo-1H-pyrazole (5.0 g, 25.8 mmol) was dissolved in DMF (50 mL), and K2C03 (4.27 g, 30.9 mmol) was added followed by 1-(chloromethyl)-4-methoxybenzene (3.86 mL, 28.4 mrnol). The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then poured into water and extracted with Et20, washed with brine, dried over sodium sulfate, filtered and concentrated to afford 4-iodo-i-(4-methoxybenzyl)-lH-pyrazole (8.3 g, 26.4 mmol, 103 % yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodopyrazole, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1613191-73-3, The chemical industry reduces the impact on the environment during synthesis 1613191-73-3, name is Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, I believe this compound will play a more active role in future production and life.

Step 2: 3-allyl 7-tert-butyl 2-amino-5, 6-dihydropyrazolo[l,5-a]pyrido[4,3-d]pyrimidine- 3, 7(8H)-dicarboxylate 4. [00239] A mixture of tert-butyl 3-(l,3-dioxolan-2-yl)-4-oxo-piperidine-l-carboxylate (100 mg, 0.3686 mmol), allyl 3,5-diamino-lH-pyrazole-4-carboxylate (67.15 mg, 0.369 mmol), KOH (5 mg, 0.0891 mmol) in dioxane (2 mL) was stirred at ambient temperature for 18h. The solid that formed was filtered and triturated in Et20 to afford compound 4 as a beige solid (lOOmg, 73%). LC-MS (M+H)+ 334.2; NMR (500 MHz, DMSO-d6) delta 8.85 (s, 1H), 6.37 (s, 2H), 6.00-6.07 (m, 1H), 5.51-5.55 (d, 1H), 5.23-5.26 (m, 1H), 4.75-4.76 (m, 2H), 4.55 (s, 2H), 3.69 (m, 2H), 3.32 (s, 2H), 2.93-2.95 (m, 2H), 1.40 (s, 9H).

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, Allyl 3,5-diamino-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); 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. 181585-93-3, name is Methyl 5-nitro-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 181585-93-3

To a solution of 2-methyl-5-nitro-2H-pyrazole-3-carboxylic acid methyl ester and 1-methyl-5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.18 g, 6.37 mmo 1) in tetrahydro furan (20 mL) at 0C was added a lithium aluminum hydride solution (1 .OM in tetrahydrofuran, 7.65 mL, 7.65 mmol) drop wise. The resulting mixture was stirred at 0C for 20 min. To this solution was added ethyl acetate (1 mL) followed by few crystals of sodium sulphate decahydrate. The resulting mixture was stirred for 30 min then filtered, the filter cake washed with ethyl acetate and the filtrate evaporated. The residue was purified by flash chromatography (silica gel, 80 g, 50% to 70% ethyl acetate in hexanes) to give 1-methyl-3-nitro-1H-pyrazol-5-yl)methanol (496 mg, 50%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (s, 3 H) 4.53 (d, J=5.67 Hz, 2 H) 5.55 (t, J=5.48 Hz, 1 H) 6.93 (s, 1 H).

The synthetic route of 181585-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BROTHERTON-PLEISS, Christine; JAIME-FIGUEROA, Saul; LOPEZ-TAPIA, Francisco Javier; LOU, Yan; OWENS, Timothy D.; WO2013/24078; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 82560-12-1, 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. 82560-12-1, name is 3-Amino-5-tert-butylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step j04: 3-Tert-butyl-1H-pyrazol-5-amine (J-III) (1 eq., 40 g) was dissolved in dilute HCl (120 ml of HCl in 120 ml of water) and mixed dropwise with NaNO2 (1.03 eq., 25 g in 100 ml) at 0-5 C. over a period of 30 min. After stirring for 30 minutes, the reaction mixture was neutralised with Na2CO3. A diazonium salt obtained by reaction of KCN (2.4 eq., 48 g), water (120 ml) and CuCN (1.12 eq., 31 g) was added dropwise to the reaction mixture within 30 min and the mixture was stirred for a further 30 min at 75 C. After complete reaction, the reaction mixture was extracted with EE (3×500 ml), the combined organic phases were dried over sodium sulfate and the solvent was removed under vacuum. The purification (SiO2, 20% EE/hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15.1% yield).

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-Amino-5-tert-butylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; US2012/115893; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 18213-75-7,Some common heterocyclic compound, 18213-75-7, name is 5-Amino-1-methyl-1H-pyrazole-4-carboxamide, molecular formula is C5H8N4O, 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 5-amino-1-methyl-1H-pyrazole-4-carboxamide (0.200 g, 1.4 mmol) in ethanol (10 mL) were added ethyl 2,2,2-trifluoroacetate (0.123 g, 8.6 mmol) and sodium hydride (60% suspension in mineral oil, 0.571 g, 14.8 mmol) with stirring at 25 C. The reaction solution was degassed with nitrogen for 3 times and stirred at 90 C for 16 h. The resulting mixture was cooled toroom temperature and concentrated under reduced pressure. The residue was partitioned between aqueous hydrochloride acid (iN, 10 mL) and ethyl acetate (20 mL). The separated aqueous layer was extracted with ethyl acetate (2 x 15 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate. The solids were filtered out and the filtrate was concentrated under vacuum. The title compound was obtained as a solid and used in next stepdirectly without further purification. MS (+ESI) m/z = 219.0.

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-1-methyl-1H-pyrazole-4-carboxamide, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori J.; CHANG, Lehua; FORSTER, Ashley; CHEN, Yili; DWYER, Michael, P.; BERGER, Richard; WANG, Ming; NANDA, Kausik K.; BUNDA, Jaime L.; SHIPE, William D.; (100 pag.)WO2016/209749; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25700-12-3, name is 3-(1H-Pyrazol-1-yl)pyridine, 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 25700-12-3, HPLC of Formula: C8H7N3

To a solution of 3-(1H-pyrazol-1-yl)pyridine (5 g, 34.4 mmol) in acetonitrile (68.9 ml) was added N-bromosuccinimide (7.97 g, 44.8 mmol). The reaction mixture was stirred at ambient temperature for 3H. The reaction mixture was diluted with EtOAc and washed with H2O, the organics were dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with 0-60% EtOAc in hexanes to afford 3-(4-bromo-1H-pyrazol-1-yl)pyridine as a tan solid (6.99 g, 91%): mp 126-127 C.; 1H NMR (400 MHz, acetone-d6) delta 9.12 (d, J=2.5 Hz, 1H), 8.64 (d, J=0.5 Hz, 1H), 8.58 (dd, J=4.7, 1.4 Hz, 1H), 8.23 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.85 (s, 1H), 7.56 (ddd, J=8.3, 4.7, 0.7 Hz, 1H); EIMS m/z 223.

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-(1H-Pyrazol-1-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW AGROSCIENCES LLC; Lowe, Christian T.; Trullinger, Tony K.; Hunter, Ricky; US2012/220453; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 360056-45-7,Some common heterocyclic compound, 360056-45-7, name is Methyl 4-amino-1H-pyrazole-3-carboxylate, molecular formula is C5H7N3O2, 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.

methyl 4-amino-1H-pyrazole-3-carboxylate (1.0 g, 7.09 mmol) and triethylamine (1.5 mL, 8.5 mmol) were stirred in dioxane (10 mL) at 0C. A solution of 2,6- dichlorobenzoyl chloride (1.5 g, 7.17 mmol) in THF (5 mL) was added dropwise until the starting material was consumed. The reaction was filtered, and the resultant solid washed with dioxane (3 x 20 mL). The filtrates were combined and used directly in the next reaction. MS (ESI) m/z 315 (M + H)+. Expected mass from chemical formula C12H9N3O3: 314.12 Da

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-1H-pyrazole-3-carboxylate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael, S.; FERGUSON, Fleur, M.; DOCTOR, Zainab, M.; (0 pag.)WO2020/5807; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 16617-46-2, 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. 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Following the procedure described in Example 1 wherein 2-methoxyethanol was used as the solvent instead of ethanol, 76percent of the product was obtained with m. p. 184-187 °C.

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

Reference:
Patent; ZENTIVA, A.S.; WO2004/37824; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 345637-71-0, The chemical industry reduces the impact on the environment during synthesis 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, I believe this compound will play a more active role in future production and life.

To a solution of (3-bromophenyl) (methyl)(((2-(piperidin-4-yl) thiazol-4-yl) methyl)imino)^6-sulfanone ; (362 mg, 0.9 mmol) in N, N-dimethylformamide (8 ml), N, N-diisopropylethylamine (0. 18 mi, 1.1 mmol) was added at 25 C. The resulting reaction mixture was stirred for 10 min, then (HATU (498 mg, 1.3 mmol) and 2-(5-methyl-3-(trifluoromethyl)- l H-pyrazoI- l -yl)acetic acid (200 mg, 1 .0 mmol) were added and stirred at 25 C for l h. The reaction was quenched with water ( 10 mL) then extracted twice with ethyl acetate ( 15mL), combined ethyl acetate layer was washed with brine ( 10 mL) and dried over sodium sulphate, concentrated and purified by preparative HPLC to obtain (3-bromophenyl)(methyl)(((2-( l -(2-(5- methyl-3-(trifluoromethyl)- l H-pyrazol- l -yI)acetyl)piperidin-4-yl)thiazol-4-yl)methyl)imino)-6- sulfanone ( 170 mg, 0.3 mmol, 32 % yield).

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, 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PI INDUSTRIES LTD.; SHANBHAG, Gajanan; SHARMA, Aditya; RENUGADEVI, G.; PABBA, Jagadish; DENGALE, Rohit Arvind; ROY, Dipankar; S.P., Mohan Kumar; BELKAR, Yogesh Kashiram; AUTKAR, Santosh Shridhar; GARG, Ruchi; VENKATESHA, Hagalavadi M; KLAUSENER, Alexander Guenther Maria; (114 pag.)WO2019/48988; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1202993-11-0, 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. 1202993-11-0, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Chloro-3-(difluoromethyl)- 1-methyl-i H-pyrazole-4-carboxylic acid (700 mg, 2.38 mmol) was dissolved in abs. dichioromethane (20 ml) in a baked-out round- bottom flask under argon and at room temperature, and oxalyl chloride (257 mg, 2.02 mmol) and catalytic amounts of N,N-dimethylformamide were added. The resulting reaction solution was then stirred under reflux conditions for 3 h. Afier cooling to room temperature, the reaction mixture was concentrated and coevaporated with a little abs. toluene.By thorough removal of solvent residues, 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (743 mg, 2.38 mmol) was obtained, which was then, without further purification, dissolved again in abs. dichloromethane (10 ml) and added dropwise to a solution, cooled to 0 C., of N,N-dimethylhydrazine (0.18 ml, 2.38 mmol) and triethylamine (0.40 ml, 2.85 mmol) in dichloromethane (10 ml) under argon. The resulting reaction mixture was stirred at room temperature for a further 30 minutes, and then water and dichloromethane were added. The aqueous phase was repeatedly extracted vigorously with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by column chromatography gave 5-chloro-3-(difluoromethyl) -N’,N’,1-trimethyl-1H-pyrazole-4-carbohydrazide in the form of a colorless solid (541 mg, 90% of theory). 5-Chloro-3-(difluoromethyl) -N?,N?,1 -trimethyl- iH-pyrazole-4-carbohydrazide (212 mg, 0.84 mmol) was dissolved in abs. tetrahydrofuran (5 ml) under argon, and sodium hydride (37 mg, 0.92 mmol, 60% purity) was added at room temperature. Stirring at room temperature for 30 minutes was followed by the addition of picolyl chloride (107 mg, 0.84 mmol), and the resulting reaction mixture was stirred under reflux conditions for 2 hours. After cooling to room temperature, sat. sodium hydrogencarbonate solution, water and dichioromethane were added. The aqueous phase was repeatedly extracted vigorously with dichioromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Final purification of the resulting crude product by colunm chromatography gave 5-chloro-3-(difluoromethyl)-N?,N?, 1 -trimethyl-N-(pyridin-2-ylmethyl)- iH-pyrazole4-carbohydrazide in the form of a colorless solid (196 mg, 68% of theory). ?H-NMR (400 MHz, CDC13 oe, ppm) 8.64 (m, iH), 7.73 (m, iH), 7.63 (m, iH), 7.36 (m, iH), 7.15-6.88 (br. t, iH, CHF2), 5.11 (s, 2H), 3.86 (s, 3H), 3.48 (s, 6H).

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, 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer CropScience Aktiengesellschaft; FRACKENPOHL, Jens; BOJACK, Guido; BRUENJES, Marco; HELMKE, Hendrik; LEHR, Stefan; BRUECHNER, Peter; TIEBES, Joerg; MOSRIN, Marc; DITTGEN, Jan; SCHMUTZLER, Dirk; DESBORDES, Philippe; (92 pag.)US2018/206498; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics