The most recent news or fashion Ark Pharm Inc. – Overview 15-Sep-2021

Ark Pharm;arkpharm;larry huang;Liangfu Huang;Ark Pharm , Inc.Ark Pharm Inc;Ark Pharm; Ark Pharm, Inc.; ARK PHARM, INC

Ark Pharm, Inc. is headquartered in IL, USA. Including custom synthesis of medicinal novel building blocks, novel templates, reference standard compounds, impurities, by-products, and other organic intermediates.
Found in 2007, Ark Pharm, Inc. is a leading supplier and manufacturer of research chemicals to pharmaceutical companies, universities, biotech companies, healthcare industries, contract research organizations etc. The founder of the company is Liangfu Huang(黄良富, larry huang)Ark Pharm specializes in the design and synthesis of medicinal building blocks, scaffolds, and advanced intermediates.

15-Sep-21 News A new synthetic route of 106368-32-5

The synthetic route of 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

These common heterocyclic compound, 106368-32-5, name is 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile, 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 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile

General procedure: A mixture of 5-amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazol-4-carbonitrile 5 (1.113 g, 5 mmol), the appropriate aldehyde (6, 5 mmol), and few drops of ethanol was added to morpholinium hydrogen sulphate (7, 0.4 g, 2 mmol). The mixture was heated in an oil bath for 5 h at 100 C. After completion of the reaction which was monitored by TLC, the solid product was filtered and crystallized from ethanol.

The synthetic route of 5-Amino-1-(4-(methylsulfonyl)phenyl)-1H-pyrazole-4-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Abdellatif, Khaled R.A.; Elsaady, Mohammed T.; Abdel-Aziz, Salah A.; AbuSabah, Ahmed H.A.; Letters in drug design and discovery; vol. 14; 8; (2017); p. 930 – 937;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

15-Sep-21 News Discovery of 1453-58-3

The synthetic route of 1453-58-3 has been constantly updated, and we look forward to future research findings.

Reference of 1453-58-3,Some common heterocyclic compound, 1453-58-3, name is 3-Methylpyrazole, molecular formula is C4H6N2, 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 B(a) 1 -Benzenesulfongammal-3 -methyrpyrazole A mixture of 3-methylpyrazole (5 g, 60.9 mmol), benzenesulfonyl chloride (8.55 mL, 67 mmol) and triethylamine (9.3 mL5 67 mmol) in acetonitrile was heated at reflux for 2 h5 allowed to cool and concentrated. EtOAc (300 mL) was added and the solution was filtered and concentrated to provide a solid residue which was crystallised from EtOAc to give the title compound as an off-white powder (Yield: 7.92 g5 58 percent).1H-NMR (DMSO-d6): delta 8.35 (d, IH)5 7.97-7.94 (m, 2H), 7.78 (tt, IH)5 7.66 (t, 2H), 6.43 (d, IH)5 2.17 (S5 3H).

The synthetic route of 1453-58-3 has been constantly updated, and we look forward to future research findings.

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

15-Sep-21 News Some tips on 4149-06-8

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 4149-06-8,Some common heterocyclic compound, 4149-06-8, name is 3-Amino-1-phenyl-1H-pyrazol-5(4H)-one, molecular formula is C9H9N3O, 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: A mixture of substituted 3-(2-aryl-2-oxoethylidene)indolin-2-one 1 (1 mmol), 1,3-dimethylurea (2, 1.2 mmol) or 5-amino-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (4, 1 mmol), PTSA·H2O (0.3 mmol), and MeCN (5 mL) was added to a 25 mL flask and reacted at 80 C (monitored by TLC) about 2 h. After completion, the mixture was cooled to r.t. and the precipitate obtained was isolated by filtration and drying. Compounds 3 or 5 were purified by recrystallization (DMF or EtOH).

The synthetic route of 4149-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dai, Lei; Shu, Ping; Wang, Zhansheng; Li, Qingyang; Yu, Qiuyu; Shi, Yanhui; Rong, Liangce; Synthesis; vol. 49; 3; (2017); p. 637 – 646;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Sep-21 News Share a compound : 821767-61-7

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, tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 821767-61-7, The chemical industry reduces the impact on the environment during synthesis 821767-61-7, name is tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, I believe this compound will play a more active role in future production and life.

Example 15 tert-butyl 4-formyl-1H-pyrazole-1-carboxylate (1.0 g) and (6-isopropylpyridin-3-yl)amine (0.694 g) were dissolved in 1,2-dichloroethane (25 mL), acetic acid (0.29 mL) and sodium triacetoxyborohydride (2.16 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give tert-butyl 4-{[(6-isopropylpyridin-3-yl)amino]methyl}-1H-pyrazole-1-carboxylate (1.46 g). 1H-NMR(CDCl3)delta: 1.26(6H,d,J=6.9Hz), 1.65(9H,s), 2.96(1H,sept,J=6.9Hz), 3.80-3.90(1H,m), 4.23(2H,d,J=6.0Hz), 6.88(1H,dd,J=3.0,8.4Hz), 6.99(1H,d,J=8.4Hz), 7.70(1H,s), 8.01(1H,d,J=3.0Hz), 8.04(1H,s).

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, tert-Butyl 4-formyl-1H-pyrazole-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Pharma Corporation; EP1852431; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September-21 News Some tips on 175137-46-9

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

Reference of 175137-46-9,Some common heterocyclic compound, 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, molecular formula is C6H9N3, 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 2,5,6-trichloronicotinonitrile (Method 44, 1.0 g, 4.8 mmol) and DIEA (0.81 g, 6.2 mmol) in n-BuOH (5 ml) was added S-cyclopropyl-lH-pyrazol-S-amme (2.3 g, 19.3 mmol). The reaction was heated to 60 0C for 2 hours, at which point the reaction was cooled to room temperature and concentrated. The resulting residue was diluted with 10 ml ACN, and stored at 00C for 1 hour. The solids that formed were then filtered, washed with cold ACN, dried and collected to give the title compound (0.62 g, 43%). MS: Calcd.: 294; Found: [M+H]+ 295.

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/82392; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September-21 News A new synthetic route of 42027-81-6

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

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. 42027-81-6, name is 2-(4-Nitro-1H-pyrazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 42027-81-6

A solution of 4-nitro-lH-pyrazole (l .Og, 8.85mmol), potassium carbonate (2eq) and 2- bromoethanol (l . leq) in acetonitrile (30mL) was heated at 60C for 18h. After cooling to rt the mixture was diluted with EtOAc and washed with H20. The organic phase was collected, dried (hydrophobic frit) and concentrated in vacuo. The crude residue was dissolved in ethanol (30mL), palladium on carbon (50mg) was added and the reaction was stirred under a balloon of hydrogen for 18h. The resulting mixture was filtered through Celite and the filtrate concentrated in vacuo to give 2-(4-amino-lH-pyrazol-l-yl)ethanol

According to the analysis of related databases, 42027-81-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELLZOME LIMITED; OXENFORD, Sally; HOBSON, Andrew; OLIVER, Kathryn; RATCLIFFE, Andrew; RAMSDEN, Nigel; WO2013/17479; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September-21 News New downstream synthetic route of 288-13-1

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.

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. 288-13-1, name is 1H-Pyrazole, A new synthetic method of this compound is introduced below., name: 1H-Pyrazole

3.40 g (0.05 mol) of pyrazoleAnd 2.8g (0.05mol) powdered KOH were added to a 100mL three-necked flask,Add 10mLDMSO as a solvent, the mixture was stirred at 80 for 30min,Then 6.25 g (0.05 mol) of 2-bromoethanol was added (added to the flask in 30 mL intervals, three times)Continue stirring for 20 ~ 30h, cooled to room temperature,After filtration, 20 mL of chloroform was added and the solution was washed with water (5 × 20 mL)Rotary drying to give a colorless transparent liquid 1-ethylpyrazole (yield: 60 ~ 70%).

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:
Patent; Henan University; Ren Tiegang; Wang Tengfei; Ma Yuan; Zhang Jingshun; Zhang Jinglai; Wang Li; (9 pag.)CN107501181; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September-21 News Extracurricular laboratory: Synthetic route of 1192-21-8

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

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. 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., category: pyrazoles-derivatives

General procedure B for the synthesis of the final product lb from intermediate E or K In a sealed tube, the bromo-intermediate E or K (0.08 mmole), t-BuONa (0.16 mmole) and the amine (0.16 mmole) were charged. The tube was filled with Argon, dry toluene (1.0 ml) was added and the mixture was stirred for 2 min. Then Pd2(dba)3 (0.0024 mmole) and t-BuXphos (0.016 mmole) were added and the vial was flushed with Argon and stirred for 2 min. The reaction mixture was then heated at 100 °C for 18h. The mixture was concentrated in vacuo and purified by flash chromatography eluting with ethyl acetate/n-heptane. To a solution of the purified product in dichloromethane (0.5ml) was added TFA (0.4 mmole) and the mixture was stirred at room temperature for 30 min. The mixture was diluted with dichloromethane and the organic layer was washed with saturated aqueous NaHC03, dried and evaporated. The crude material was purified by chromatography on NH2-silica using dichloromethane to give the pure final product lb. In case of using intermediate E, the coupling product was deprotected using CF3COOH as described above to give the pure final product lb.Example 36(S)-2-Amino-6-[2-fluoro-5-(2-methyl-2H-pyrazol-3-ylamino)-phenyl]-3,5,5,6-tetramethyl- 5,6-dihydro-3H-pyrimidin-4-oneThe coupling of [(S)-4-(5-bromo-2-fluoro-phenyl)- 1,4,5, 5-tetramethyl-6-oxo- 1,4,5, 6- tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (intermediate E8) and 2-methyl-2H- pyrazol-3-ylamine according to procedure B followed by deprotection yielded the title compound as a pale brown waxy solid. MS (ESI): m/z = 359.2 [M+H]+.

According to the analysis of related databases, 1192-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; SIENA BIOTECH S.P.A; BANNER, David; GABELLIERI, Emanuele; GUBA, Wolfgang; HILPERT, Hans; HORNSPERGER, Benoit; HUMM, Roland; MAUSER, Harald; MAYWEG, Alexander, V.; NARQUIZIAN, Robert; PINARD, Emmanuel; ROGERS-EVANS, Mark; WOLTERING, Thomas; WOSTL, Wolfgang; WO2012/19966; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

September 15, 2021 News Application of 1280210-79-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Synthetic Route of 1280210-79-8, 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. 1280210-79-8 name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, 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.

To a solution of tert-butyl 4,6-dihydropyrrolo[3,4- c]pyrazole-5(2H)-carboxylate (15.0 g, 71.8 mmol) in DMF (150 mL) was added NaH (60% in mineral oil) (8.6 g, 215.4 mmol) while the reaction mixture was cooled with an ice bath. When the addition was complete, the resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this point, l-bromo-2- methoxyethane (19.8 g, 143.6 mmol) was added into the reaction mixture, and stirring was continued at room temperature for 2 h. The reaction mixture was then quenched with water (300 mL), and extracted with EtOAc (150 mL x 3). The combined organic layer was washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 122 and 122-A (19.0 g, 99%) as a colorless oil. MS 268.2 [M + H]+. [0072] Synthesis of 123 and 123-A. To a solution of 122 and 122-A (6.5 g, 24.3 mmol) in DCM (60 mL) cooled with an ice bath was added TFA (30 mL). The reaction mixture was stirred at room temperature for 1 h, whereupon the solvent was removed in vacuo to give 123 and 123-A as a crude product mixture which was used directly in the next step without further purification. MS 168.1 [M+H]+. (0114) [0073] Synthesis of 124 and 124-A. To a solution of 123 and 123-A (24.3 mmol, crude product from last step) and A4 (9.3 g, 20.3 mmol) in DMSO (200 mL) was added Na2C03 (21.5 g, 203 mmol), and the reaction mixture was stirred at room temperature for 4 h. The mixture was then diluted with water (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine (100 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 30 : 1) to give a mixture of 124 and 124-A (4.5 g, 50%) as a yellow solid. MS 411.0, 413.1 [M+H]+. Example 8. Synthesis of Compound 8 (0126) (0127) [0081] Synthesis of 129 and 129-A. A mixture of 124 and 124-A (350 mg, 0.85 mmol), 2-fluorophenylboronic acid (143 mg, 1.02 mmol) and K2CO3 (352 mg, 2.55 mmol) in dioxane/H20 (10 mL/2 mL) was treated with Pd(PPh3)4 (49 mg, 0.04 mmol) under a N2 atmosphere. The reaction mixture was stirred at 90 C for 3 h and then concentrated in vacuo. The crude residue was taken up in EtOAc (30 niL), and the resulting solution was washed with brine (10 mL x 3). The organic layer was dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by Prep-TLC (PE : EA = 5: 1) to give a mixture of 129 and 129-A (300 mg, 83%) as a yellow solid. MS 427.2 [M + H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; RODIN THERAPEUTICS, INC; FULLER, Nathan, Oliver; LOWE, John, A.; (45 pag.)WO2019/32528; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics