Tag: M.W:200-300

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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H15N3O2

Synthesis of 244-A. To a solution of tert-butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)- carboxylate (1.40 g, 6.70 mmol) in DCM (10 mL) was added TFA (3 mL) dropwise under ice bath. Then the solution was stirred at room temperature 1 h. The solvent was removed in vacuo to give 244- A as a crude product

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; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 83-10-3, The chemical industry reduces the impact on the environment during synthesis 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, I believe this compound will play a more active role in future production and life.

Take raw material 1 (0.01mol) and raw material p-aminophenol 2 (0.01mol) was dissolved in DMF 15mL, was addedEDC.HCl (5.75 g, 0.03 mmol) was added and the reaction stirred at room temperature for 8 h. After the reaction was completed, water was added to the reaction solution to precipitate a white solid After stirring for 15 min, the filter cake was washed with water to neutrality and dried in vacuo to give a white solid. Intermediate 3 was obtained in 94% 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, 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Li Jianqi; Huang Daowei; Wang Wenya; Zhang Zhiguo; Jiang Ling; (45 pag.)CN107286140; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1146629-77-7, name is (4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, 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 1146629-77-7, Formula: C15H17N5O2

To a solution (15 mL) of 37 (514 mg, 1.72 mmol, preparation described in Lin, Q. et al. Org. Lett., 2009, 11, 1999-2002) in acetonitrile was added 44 (537 mg, 4.29 mmol) , Then DBU (540 muL, 3.61 mmol) was added. The reaction was stirred at room temperature for 15 h and then concentrated under reduced pressure. The resulting crude mixture was diluted with water and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with 1 N HCl, dried (Na 2 SO 4), filtered and concentrated under reduced pressure. Purification by normal phase column chromatography (SiO 2, 0 to 60% ethyl acetate / hexane) gave (+/-) 45 as a white foam (368 mg, 50%)

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-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Concert Pharmaceuticals Inc.; Zhou, Haibing; Peng, Xueke; Hu, Zhiye; Ning, Wentao; Dong, Chune; (43 pag.)JP2018/172421; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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. Quality Control of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate

Under argon, the goodsN-Boc-protected pyrazolopyrrolidine (1) (1 eq.) Was mixed in dry acetonitrile and sodium hydride (1.2 eq.) Was added slowly with ice bath cooling. The reaction mixture was stirred for 2 hours at room temperature.The resulting white suspension, iceUnder cooling in the bath, the product trideuteromethanesulfonyl chloride (methanesulfonyl chloride-D3) (2) (2 equivalents) is added slowly.After the addition was completed, the mixture was further stirred at 25 C for 1 hour.LC-MS and TLC showed that the basic reaction of the intermediate was completed.The reaction was quenched by addition of water and extracted with methylene chloride. The organic phases were combined and washed with water.Dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography to give tert-butyl 1- (trideuteromethylsulfonyl) -4,6-dihydropyrrolo [3,4-c] pyrazole- 5 (1H) Ester.

The synthetic route of tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Ji Bell Pharmaceutical Co., Ltd.; Zhenjiang Sheng’an Pharmaceutical Co., Ltd.; Geng Zhongyi; Chen Xinghai; (20 pag.)CN107337674; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 92525-10-5, name is 3-Iodo-1-methyl-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 92525-10-5, Quality Control of 3-Iodo-1-methyl-1H-pyrazole

H) 3-amino-5-(2-methylcyclohexyl)-7-(1-methyl-1H-pyrazol-3-yl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one A mixture of 3-amino-7-bromo-5-(2-methylcyclohexyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step G (200 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (861 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (22.0 mg), potassium acetate (121 mg) and N,N-dimethylformamide (3.0 mL) was heated with microwave irradiation at 110C for 5 hr. The reaction mixture was cooled to room temperature, and 3-iodo-1-methyl-1H-pyrazole (384 mg), aqueous sodium carbonate solution (2 M, 0.610 mL) and tetrakis(triphenylphosphine)palladium(0) (71.0 mg) were added thereto at room temperature. The reaction mixture was heated with microwave irradiation at 140C for 1 hr. The reaction mixture was cooled to room temperature, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/dichloromethane) to give the title compound (51.0 mg). 1H NMR (400 MHz, CDCl3) delta 0.78-0.88 (3H, m), 1.24-2.04 (9H, m), 3.96 (3H, brs), 4.74-4.77 (2H, m), 6.40-6.45 (1H, m), 7.33-7.37 (1H, m), 7.39-7.40 (1H, m), 10.45 (1H, brs). MS (ESI+): [M+H]+327.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-methyl-1H-pyrazole, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

51516-67-7, name is 5-Amino-1-(4-chlorophenyl)-1H-pyrazole-4-carbonitrile, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C10H7ClN4

General procedure: Equimolar portionsof the intermediate compounds 1 (1 mmol) and the intermediatecompounds 3 (1 mmol) were dissolved in approximately 8 mL ofethanol. The reaction solution was allowed to stir at 80 8C for 2 huntil the reaction was complete. The reaction was monitored byTLC. Mostly, a precipitate formed and was then collected by suctionfiltration.

The synthetic route of 51516-67-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, 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 10250-64-3, Recommanded Product: 10250-64-3

(R) -1,1,1-trifluoro-2-((S) -5-methyl-5,6,7,8-tetrahydro [1,2,4] triazolo [4] obtained in the previous step , 3-a] pyrazin-3-yl) propan-2-ol dihydrochloride (39 mg) and 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid (29.1 mg) were added to dimethylformamide (0. 6mL). below freezing,To this mixture was added diisopropylethylamine (83 muL) and HATU (55 mg),Stir at room temperature overnight.Under ice-cooling, a saturated aqueous sodium hydrogen carbonate solution and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate.Organic layer with saturated aqueous sodium bicarbonate solution,Washed sequentially with water and saturated aqueous sodium chloride solution. The organic layer was dried with sodium sulfate.Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure.The obtained residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1 to chloroform: methanol = 20: 1).Add ethyl acetate and hexane to the resulting solid,Stir at room temperature for 1 hour.By filtering the solid,The title compound (41.7 mg) was obtained.

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, 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; japan Tobacco Inc.; Maeba, Takaki; Sazawa, Koichi; Kotoku, Masayuki; Masuo, Ritsuki; Motoda, Dai; Yamaoka, Nobutaka; (126 pag.)JP2019/131544; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 39806-90-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 39806-90-1 as follows.

Example 58. Synthesis of (R)-5-(l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6- dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepin-8-yl)pyridin-2-amine (Compound 76). The title compound was synthesized by the following scheme:[00393] (R)-8-bromo-l,4-dimethyl-6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [l,2,4]triazolo[4,3-d][l,4]diazepine (Step 1). A mixture of (R)-8-bromo-l,4-dimethyl-5,6- dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (292 mg, 1 mmol), 4-iodo-l-methyl- lH-pyrazole (312 mg, 1.5 mmol), copper (I) iodide (58 mg, 0.3 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium phosphate (424 mg, 2 mmol) in dimethyl sulfoxide (10 mL) was heated at 150C for 14 hours under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (20 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give (R)-8-bromo-l,4-dimethyl- 6-(l-methyl-lH-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b] [1,2,4] triazolo[4,3-d][l,4]diazepine which was used in the next step without further purification. LRMS (M+H)+: calcd 372.07; found 372.

According to the analysis of related databases, 39806-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
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. 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

A mixture of (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (25 uL, 0.158 mmol), copper (I) iodide (4.0 mg, 0.021 mmol), potassium phosphate tribasic (69.7 mg, 0.328 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (42.7 mg, 0.204 mmol) and [(3R,3aR,6R,6aS)-3-(1-allyl-6-chloro-5-iodo-imidazo[4,5-b]pyridin-2-yl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (84 mg, 0.145 mmol) in dioxane (1.0 ml) was degassed (3×) and placed under nitrogen before being heated to 100 C. After 6 hours, the reaction mixture was diluted with EtOAc (30 ml), washed with water (20 ml), brine (10 mL), dried over MgSO4, filtered, and evaporated under reduced pressure to give an oil. The oil was purified on preparative silica plates (1×1000 u developed with 1:1 EtOAc/hexanes). The resulting solid (86.4 mg, 0.131 mmol) was dissolved in TFA (1.0 mL) and DCM (1.0 mL) and was stirred at room temperature. After 1 hour, the reaction mixture was evaporated to give an oil, and which was lyophilized from ethanol and benzene to give the title compound as a solid. LC-MS: calculated for C26H35ClN6O4Si 558.22 observed m/e: 559.27 (M+H)+ (Rt 1.15/2 min).

The synthetic route of 1280210-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; APGAR, James M.; ARASAPPAN, Ashok; BIFTU, Tesfaye; CHEN, Ping; FENG, Danqing; GUIDRY, Erin; HICKS, Jacqueline; KEKEC, Ahmet; LEAVITT, Kenneth; LI, Bing; MCCRACKEN, Troy; SEBHAT, Iyassu; QIAN, Xiaoxia; WEI, Lan; WILKENING, Robert; WU, Zhicai; Merck Sharp & Dohme Corp.; Apgar, James M.; Arasappan, Ashok; Biftu, Tesfaye; Chen, Ping; Feng, Danqing; Guidry, Erin; Hicks, Jacqueline D.; Kekec, Ahmet; Leavitt, Kenneth J.; Li, Bing; McCracken, Troy; Sebhat, Iyassu; Qian, Xiaoxia; Wei, Lan; Wilkening, Robert R.; Wu, Zhicai; US2015/284411; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (5) (57 mg, 0.250 mmol) in DCM (6.0 mL) was added saturated aq NaHCO3 solution (4.0 mL) The mixture was stirred vigorously and was cooled to 0 C. and trichloromethylchloroformate (0.091 mL, 0.750 mmol) was added in one portion. The resulting mixture was stirred at 0 C. for 1.5 hr. The biphasic mixture was separated and the organic extract was dried and the solvents removed under reduced pressure to afford an oil, which was dried under high vacuum, at 35 C. for 35 min. The resulting oil was taken up into THF (5.0 mL), and then added to 4-(1-(4-aminonaphthalen-1-yloxy)ethyl)pyridin-2-amine (39) (81 mg, 0.290 mmol). DIPEA (179 muL, 1.029 mmol) was added, and the reaction mixture was stirred at RT for 16 hr. Water (15 mL) and EtOAc (10 mL) were added to the reaction mixture and the layers were separated. The aq layer was extracted with EtOAc (15 mL). The combined organic extracts were washed with brine (20 mL), dried and the solvents removed under reduced pressure. The resulting residue was dissolved in MeOH (5.0 mL) and AcOH (2.0 mL) and subjected to SCX capture and release. The crude mixture was purified by column chromatography (SiO2, 12 g, 0-10% MeOH in DCM, gradient elution) to give the title compound, Intermediate G, (63 mg, 38%) as a beige powder: m/z 535 (M+H)+ (ES+).

The chemical industry reduces the impact on the environment during synthesis 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RESPIVERT LIMITED; Charron, Catherine Elisabeth; Fenton, Robert; Crowe, Scott; Ito, Kazuhiro; Strong, Peter; Rapeport, William Garth; (78 pag.)US2016/45512; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics