Tag: M.W:200-300

Adding a certain compound to certain chemical reactions, such as: 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-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 1280210-79-8, Product Details of 1280210-79-8

Under N2 protection and a condition free of water and oxygen, Intermediate 2 (1000 mg, 4.78 mmol) was dissolved in N,N-dimethylformamide (15 ml), which was cooled to -15C, and sodium bis(trimethylsilyl)amide (4.78 mL, 2 mol/L, 9.56 mmol) was added, followed by stirring for 30 min, and S-cyclopentylsulfonyl chloride (1.37 g, 8.13 mmol) was added dropwise, followed by reaction for 16 hours at -15C. The temperature was raised to 0C, and the reaction was quenched by addition of water (20 ml) to the reaction solution, which was then extracted with ethyl acetate (20 ml*2). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated, re-dissolved in tetrahydrofuran (20 ml), and cooled to a temperature between -10C and 0C, potassium t-butoxide (85 mg, 0.76 mmol) was added, and the reaction was allowed to proceed for 24 hours at this temperature. After the reaction was completed, a saturated aqueous solution of ammonium chloride (10 ml) and water (10 ml) were added. The solution was extracted with ethyl acetate (20 mL*3). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate (v/v) = 5:1) to obtain a white solid 6a (800 mg, yield 62%).

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:
Patent; Sichuan Haisco Pharmaceutical Co., Ltd.; ZHANG, Chen; WANG, Jianmin; LI, Caihu; WEI, Yonggang; (64 pag.)EP3159344; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 141573-95-7, A common heterocyclic compound, 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, molecular formula is C8H10F2N2O2, 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.

Example 1Ethyl 5-chloro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate (III-1) 20.25 g (100 mmol) of ethyl 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylate and 40 ml of SO2Cl2 are placed under argon and the mixture is heated to 60 C. and stirred at this temperature for 8 hours. After diluting the mixture with ethyl acetate, washing with water and removing the solvent under vacuum, 21 g of the product are obtained with an HPLC purity of 94%. M.p. 37-39 C.1H NMR (CDCl3): delta=7.1 (1H, t), 4.3 (q, 2H), 3.9 (s, 3H), 1.4 (t, 3H) ppm.19F NMR (CD3CN): delta=-114.9 (2F, t) ppm.

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; Bayer CropScience AG; US2011/288305; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39806-90-1, name is 4-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 39806-90-1, Recommanded Product: 4-Iodo-1-methyl-1H-pyrazole

To a mixture of Cul (6 mg, 0.033 mmol, 0.2 equiv.), 4-iodo-l -methyl- 1H- pyrazole (41 mg, 0.195 mmol, 1.2 equiv.) and K2CO3 (90 mg, 0.651 mmol, 4.0 equiv.) were added methyl 3-((4-chlorobenzyl)amino)-2-oxopyrrolidine-3-carboxylate (46 mg, 0.163 mmol, 1.0 equiv.) in anhydrous l,4-dioxane (2 mL) and N,N-dimethylethylenediamine (4 m^, 0.033 mmol, 0.2 equiv.). The resulting mixture was flushed with nitrogen, sealed, heated in an oil bath at 115 C for 18 h, cooled to room temperature, filtered through a syringe filter, and purified with reverse phase HPLC using 10% – 100% ACN / water (both with 0.1% formic acid; Phenomenex Gemini C18 5 micron column) to provide 8 mg (14%) of methyl 3- ((4-chlorobenzyl)amino)-l-(l-methyl-lH-pyrazol-4-yl)-2-oxopyrrolidine-3-carboxylate. LRMS (APCI) m/z 363.2 (M+H).

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:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; ASHCRAFT, Luke W.; LAU, Kevin; (455 pag.)WO2020/47447; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 398491-61-7, 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. 398491-61-7 name is tert-Butyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-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.

Intermediate EKIII-2): tert-Butyl 3-amino-6,6-dimethyl-1-{[2- (trimethylsilyl)ethoxy]methyl}-4.6-dihydropyrrolo[3,4-c]pyrazole-5(1 H)-carboxylateMe3SiTo the mixture of the intermediate EKII) (87g), methylene chloride (1.74L) and diisopropylethylamine (87g) at O0C were added 2-(trimethylsilyl)ethoxymethyl chloride (63g) drop wise at O0C (1 hour addition). The reaction mixtures were stirred at room temperature over night. The reaction was a light brown solution. Then the mixture was concentrated to give a light yellow/brown oil and the residue was mixed with ethyl acetate and the salts were filter off. The mixture was purified with silica gel (2:1 to 1:1 EtOAc/Hexane with 0.5% of TEA) to afford the regioisomers EKIII-2) (24g, >90% purity by HPLC) and E(III-D (1Og, >98% purity by HPLC). 1H NMR (400 MHz, CD3OD) ppm – 0.03 (s, 9H) 0.88 (t, J=8.2 Hz, 2H) 1.48 and 1.53 (s, 4.5H each, a total of 9H), 1.70 (s, 3H), 1.72 (s, 3H), 3.56-3.62 (m, 2H), 4.24-4.26 (m, 2H), 5.16 (s, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-5(1H,4H,6H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; WO2008/125945; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1280210-79-8,Some common heterocyclic compound, 1280210-79-8, name is tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, molecular formula is C10H15N3O2, 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 vial was charged with (3R,3aR,6R,6aR)-6-[5-(4-bromophenyl)-6-chloro-1-(2-trimethylsilylethoxymethyl)-imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (501.8 mg, 0.861 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (240.3 mg, 1.148 mmol), tripotassium phosphate (581.6 mg, 2.74 mmol), and copper(I) iodide (37.2 mg, 0.195 mmol). The reaction was evacuated (3×) and backfilled with nitrogen. Trans-N,N?-dimethylcyclohexane-1,2-diamine (55 mul, 0.348 mmol) and dioxane (1.7 ml) were added to the vial to give a hazy suspension, which was heated to 100 C. for 24 h. The reaction mixture was then cooled to room temperature and partitioned between EtOAc (100 ml) and water (100 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a pale green residue. Flash chromatography of the residue utilizing a 40 g silica RediSep Rf column and employing a 0-100% EtOAc/hexane gradient afforded a mixture of the two pyrazole linked regioisomers as a pale amber foam. LC-MS: calculated for C34H43ClN6O7Si 710.27 observed m/e: 711.29 (M+H)+ (Rt 1.30/2 min)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, its application will become more common.

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

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. 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Iodo-1-methyl-1H-pyrazole

To a solution of 4-amino- 1 -methyl -pyrrolidin-2-one (100 mg, 0.88 mmol) in toluene (2 ml) was added 4-iodo- 1 -methyl-pyrazole (200 mg, 0.96 mmol), sodium tert-butoxide (168 mg, 1.75 mmol) and [2-(2-aminoethyl)phenyl]-chloro-palladium;ditert-butyl-[2- (2,4,6- triisopropylphenyl)phenyl]phosphane (also known as tBuXPhos Pd Gl) (60 mg, 88 pmol), then the mixture was stirred at 100 C for 3 h. The mixture was concentrated under reduced pressure. The residue was purified by prep-HPLC (column: Waters Xbridge Prep OBD C18 5pm 150×30; mobile phase: [water (0.1 % TFA) – ACN]; B: 1 – 30 %,l0 min) to give the title compound as colourless gum (Y = 20 %). ‘H NMR (400 MHz, methanol-*) d ppm 7.63 (s, 1H), 7.43 (s, 1H), 4.17 – 4.05 (m, 1H), 3.87 (s, 3H), 3.84 – 3.76 (m, 1H), 3.43 (dd, J= 3, 11 Hz, 1H), 2.90 – 2.79 (m, 4H), 2.41 (dd, j= 3, 18 Hz, 1H).

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; NODTHERA LIMITED; HARRISON, David; WATT, Alan Paul; BOCK, Mark G.; (334 pag.)WO2019/121691; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, 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. name: 4-Bromo-1-(tert-butyl)-1H-pyrazole

General procedure: Pd(dppf)Cl2 (1.45 g, 1.98 mmol) was added to a mixture of 4-bromo-1-(tert-pentyl)-1H-pyrazole (8.6 g, 39.61 mmol), Intermediate 4 (6.56 g, 47.53 mmol), K2CO3 (10.95 g, 79.22 mmol), dioxane (90 mL), and H2O (45 mL) at rt under N2. The mixture was degassed with 3 vacuum/N2 cycles, heated at 80 C. for 4 h, cooled to rt, and then poured into H2O (100 mL). The precipitate was filtered off. The filtrate was diluted with ethyl acetate (200 mL) and H2O (100 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered, concentrated, and then purified by silica gel chromatography (CH2Cl2/CH3OH=100/1?30/1) to give 2.7 g of an impure red solid. HCl in CH3OH (4M, 30 mL) was added. The solution was stirred at rt for 2 h, concentrated, diluted with ethyl acetate (15 mL), and then stirred overnight. The solids were filtered, washed with ethyl acetate (10 mL), and dried to give 4-(1-(tert-pentyl)-1H-pyrazol-4-yl) pyridin-2-amine hydrochloride (3.1 g). This material was dissolved in H2O (5 mL). Aqueous potassium carbonate (2 M, 8 mL) was added slowly until pH=9-10. The mixture was extracted with ethyl acetate (20 mL×6). The combined organics were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated to give 4-(1-(tert-pentyl)-1H-pyrazol-4-yl) pyridin-2-amine (2.35 g, 90%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): delta 8.24 (s, 1H), 7.84-7.83 (m, 2H), 6.75-6.73 (m, 1H), 6.60 (s, 1H), 5.74 (s, 2H), 1.87-1.81 (m, 2H), 1.52 (s, 6H), 0.62 (t, 3H); LCMS: 231.2 [M+H]+.

The synthetic route of 70951-85-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Metacrine, Inc.; SMITH, Nicholas D.; GOVEK, Steven P.; DOUGLAS, Karensa L.; LAI, Andiliy G.; US2020/102308; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 285984-25-0, 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. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of CDI (973 mg, 6.00 mmol) in dry DCM (10.0 mL) under N2 was added Intermediate A1 (1.38 g, 6.00 mmol) as a solid, in four equal portions, over 10 min and the resulting solution maintained at RT for 16 hr. An aliquot of this solution (473 muL, 0.284 mmol) was added to a suspension of Intermediate G2 (100 mg, 0.296 mmol) in anhydrous DCM (5.0 mL) and the reaction mixture kept at RT for 24 hr. The reaction mixture, in its entirety, was purified by flash column chromatography (SiO2, 40 g, MeOH in DCM, 0-10%, gradient elution) to afford the title compound, Example 16, as a yellow solid (108 mg, 59%); Rt 4.60 min (Method 1 basic); m/z 594 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1.27 (9H, s), 2.39 (3H, s), 3.36 (3H, s), 4.06 (2H, s), 5.39 (2H, s), 6.35 (1H, s), 7.22 (1H, d), 7.30 (1H, dd), 7.36 (2H, m), 7.44 (2H, m), 7.60 (1H, dd), 7.64 (1H, d), 8.24 (1H, br s), 8.27 (1H, dd), 8.34 (1H, dd), 8.59 (1H, br s), 8.89 (1H, br s), 8.92 (1H, dd), 10.04 (1H, br s).

The synthetic route of 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; King-Underwood, John; Hardy, George; Murray, Peter John; Williams, Jonathan Gareth; Onions, Stuart Thomas; US2013/29990; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 70951-85-8, The chemical industry reduces the impact on the environment during synthesis 70951-85-8, name is 4-Bromo-1-(tert-butyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of 4-bromo-1-(1 ,1-dimethylethyl)-1 H-pyrazole (2.4g, 1 1.82mmol), 4.4.4′.4′.5.5.5′.5′-octamethyl-2,2′-bi-1 ,3,2-dioxaborolane (3.00g, 1 1.82mmol), potassium acetate (2.90g, 29.5mmol), tris(dibenzylideneacetone)dipalladium (0) (0.108g, 0.1 18mmol), 2-(dicyclohexylphosphino)-2′.4′,6′-triisopropylbiphenyl (0.225g, 0.473mmol) in 1 ,4-dioxane (30ml) was degassed with nitrogen. The reaction mixture was spilt into 2 microwave vials and heated at 1 10C in a microwave for 1 .5h. There was no starting material remaining so the reactions were filtered through a bond elut reservoir and the residue was washed with ethyl acetate. The filtrate was concentrated in vacuo to yield the crude product. This was dissolved in DCM and purified through silica (50g) eluting with 0-50% ethyl acetate in DCM gradient. Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a beige solid (1.68g).LCMS (Method B): Rt = 1 .08min, MH+ = 250.8

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-1-(tert-butyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; ATKINSON, Francis Louis; BARKER, Michael David; DOUAULT, Clement; GARTON, Neil Stuart; LIDDLE, John; PATEL, Vipulkumar Kantibhai; PRESTON, Alexander George Steven; WILSON, David Matthew; WO2011/134971; (2011); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

497832-99-2, name is 4-Bromo-1-methyl-3-(trifluoromethyl)-1H-pyrazole, 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. Recommanded Product: 497832-99-2

A mixture of 286 tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)silane (1.0 g, 3.0 mmol), 288 4-bromo-1-methyl-3-(trifluoromethyl)-1H-pyrazole (822 mg, 3.6 mmol), and Pd(dppf)Cl2 (110 mg, 0.15 mmol), in a mixture of 80 acetonitrile (12 mL) and a 1 M aqueous solution of 179 NaHCO3 (5.4 mL) was bubbled with N2 for 1 min and then heated in a microwave reactor to 130 C. for 15 min. After cooling to rt, a 1 M solution of 289 TBAF in 10 THF (3 mL, 3 mmol) was added and the mixture was stirred at rt for 5 h, then diluted with CH2Cl2 and washed with water, brine, dried (MgSO4) and evaporated. The residue was purified (FCC, SiO2, 10-60% EtOAc/heptanes) to provide the 281 title compound (445 mg, 61% yield) as an off-white solid. 1H NMR (300 MHz, CDCl3) delta 7.45 (d, J=1.00 Hz, 1H), 7.28 (d, J=1.00 Hz, 2H), 6.88 (d, J=8.56 Hz, 2H), 5.16 (br s, 1H), 3.99 (s, 3H). [M+H]=243.2.

The synthetic route of 497832-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dart NeuroScience, LLC; Bookser, Brett; Botrous, Iriny; Branstetter, Bryan; Dyck, Brian; Weinhouse, Michael; US2019/177327; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics