Tag: M.W:100-200

Related Products of 151049-87-5, These common heterocyclic compound, 151049-87-5, name is 3-Bromo-1-methyl-1H-pyrazole, 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.

(2,6-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (6.0 g, 22.2 mmol, 1.0 eq.), 3-bromo-1-methyl-1H-pyrazole (4.29 g, 26.7 mmol, 1.2 eq.), potassium carbonate (6.23 g, 44.4 mmol, 2.0 eq.) and tetrakis(triphenylphosphine)palladium(0) (487 mg, 0.67 mmol, 0.03 eq.) were combined into a reaction flash under an inert atmosphere. Degassed 1,4-dioxane (92.5 mL) and water (18.5 mL) were added. After 16 h at 100 C., the reaction mixture was diluted with water and extracted with IPA/CHCl3 (1:3) (3*). The combined organic extracts were concentrated under reduced pressure. Purification using flash column chromatography on silica gel with 0-70% MeCN/DCM provided the title compound (3.9 g, 78% yield). 1H-NMR (400 MHz, DMSO-d6) 7.77 (d, J=2.3 Hz, 1H), 7.48-7.42 (m, 2H), 6.83 (d, J=2.3 Hz, 1H), 5.22 (t, J=5.6 Hz, 1H), 4.49 (d, J=5.5 Hz, 2H), 3.88 (s, 3H); ES-MS [M+H]+=225.4.

Statistics shows that 3-Bromo-1-methyl-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 151049-87-5.

Reference:
Patent; Vanderbilt University; Lindsley, Craig W.; Conn, P. Jeffrey; Engers, Darren W.; Bender, Aaron M.; US2020/131159; (2020); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

146941-72-2, name is 4-Bromo-1-methyl-1H-pyrazol-3-amine, 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. Formula: C4H6BrN3

General procedure: A soln. of amine BB-34 (1 eq) and aldehyde or ketone BB-12 (1.05 to 1.1 eq) in MeOH (2 to 4 mL/mmol) was stirred for 1 h at RT. NaBI-U (1.6 to 2 eq) was added portionwise at 0C and the rxn mixture was stirred at a given temperature for a given time (see Table 52). It was quenched with H2O at 0C and extracted with EtOAc. The combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. When necessary, the crude was purified by CC using EtOAc/MeOH

The synthetic route of 146941-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 1151802-23-1, The chemical industry reduces the impact on the environment during synthesis 1151802-23-1, name is 4-Bromo-1-cyclopropyl-1H-pyrazole, I believe this compound will play a more active role in future production and life.

Bis(pinacolato)diboron (330 mg, 1.3 mmol), NaOAc (262 mg, 3.2 mmol), and Pd(dppf)Cl2-dichloromethane complex (89 mg, O. l lmmol) were combined in a microwave vial. 4-Bromo-l -cyclopropyl- lH-pyrazole and DMF (4 mL) were added and the vial was flushed with argon and sealed. The reaction mixture was heated in a microwave for 60 min at 150 0C. The reaction was diluted with 10 mL water and extracted 3 x 10 mL with EtOAc. The combined organic layers were dried over Na2Stheta4 and concentrated to yield 120 mg of the title compound as a dark oil, m/z 235.4 [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-Bromo-1-cyclopropyl-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEMIEUX, Rene, Marc; BRUNETTE, Steven, Richard; HORAN, Joshua, Courtney; KOWALSKI, Jennifer, A.; LAWLOR, Michael, David; MCKIBBEN, Bryan; MILLER, Craig, Andrew; BARBOSA, Antonio, J.M.; WO2010/141273; (2010); 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. 89501-90-6, name is 1-Methyl-1H-pyrazole-3-sulfonyl chloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H5ClN2O2S

General procedure: 0.20 mmol of theappropriately substituted sulfonyl chloride was dissolved in dry pyridine (2mL) and 0.24 mmol of5-amino-7-alkyl-2-[(methylcarbamoyl)amino]-1-benzothiophene-3-carboxamide (19a-c)was added to the solution. The reaction mixture was stirred until the startingamine disappeared completely according to TLC analysis (2-3 hours). 1.0 Mhydrochloric acid was added, the precipitate was filtered off, washed withwater and dried on air. The crude product was dissolved in hot THF (80-100 mL)and decolorized with activated charcoal. The mixture was filtered through celite,washed with ethyl acetate (2 x 40 mL), and the filtrate was evaporated underreduced pressure. The residue was solidified under diisopropyl ether, and theprecipitate was filtered off and dried on air.

The synthetic route of 89501-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gyulavari, Pal; Szokol, Balint; Szabadkai, Istvan; Brauswetter, Diana; Banhegyi, Peter; Varga, Attila; Marko, Peter; Boros, Sandor; Illyes, Eszter; Szantai-Kis, Csaba; Kreko, Marcell; Czudor, Zsofia; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 19; (2018); p. 3265 – 3270;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 637336-53-9, 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. 637336-53-9, name is Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Isoamyl nitrite (1 .3 ml_, 9.67mmol) was added drop-wise to a suspension of methyl 4- amino-1 -methyl-1 H-pyrazole-3-carboxylate (p70, 1 g, 6.45 mmol), CuBr2 (1 .44 g, 6.45 mmol) and CuBr (924 mg, 6.45 mmol) in MeCN (25 ml_). The resulting mixture was stirred at 80 C for 2 hrs. After cooling to RT the volatiles were evaporated under vacuum and the residue was purified by FC on S1O2 column (eluting from cHex to 40% EtOAc) to afford methyl 4-bromo- 1 -methyl- 1 H-pyrazole-3-carboxylate (p71 , 500 mg, y= 35 %) as brown solid. MS (mlz): 220.9 [MH]+

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, Methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; CREMONESI, Susanna; SEMERARO, Teresa; TARSI, Luca; GIBSON, Karl Richard; (116 pag.)WO2019/81939; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 20154-03-4, 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. 20154-03-4, name is 3-(Trifluoromethyl)-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows.

Compound Bl (3 g; 8.43 mmol), 3-trifluoromethylpyrazole (3.44 g; 25.28 mmol), potassium carbonate (7 g; 50.58 mmol) and copper iodide (322 mg; 1.69 mmol) were suspended in 50 mL of nitrobenzene in a stream of nitrogen, and the temperature of the water bath was raised to 200°C under stirring. The mixture was stirred for 2 hours under heating, and then cooled to room temperature. Insolubles were removed by sellaite filtration, and the solvent of the filtrate was distilled off under reduced pressure. Purification of the residue through a silica gel column (hexane:ethyl acetate = 9:1) yielded 2.57 g (yield: 65.4percent) of compound Cl as a colorless liquid. Phosphorescence lambdamax = 452 nm (dichloromethane solution).

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

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; WO2006/98505; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25016-11-9, 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. 25016-11-9 name is 1-Methyl-1H-pyrazole-4-carbaldehyde, 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.

Acetic acid (101muL; 1.76mmol) was added under nitrogen atmosphere, at rt to a solution of intermediate 27 (430mg; 0.88mmol) and 1-methyl-1H-pyrazole-4- carbaldehyde( CAS [25016-11-9]) (194mg; 1.76mmol) in THF (15mL). The mixture was stirred at rt for 3 hours. Subsequently, NaBH(OAc)3 (561mg; 2.65mmol) was added portionwise and the mixture was stirred at rt for 15 hours. The mixture was poured into a mixture of water, and a 10% solution of K2CO3. EtOAc was added and stirred at rt for 15 min and extracted with EtOAc (x2). The organic layers were combined, dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography over silica gel (Stationary phase: irregular SiOH 15-40mum 24g GRACE, Mobile phase: Gradient from 0.1% NH4OH, 97% DCM, 3% MeOH to 0.1% NH4OH, 95% DCM, 5% MeOH). The fractions containing product were collected and evaporated to dryness yielding 420 mg (82%) of intermediate 28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methyl-1H-pyrazole-4-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PATRICK, Aaron, Nathaniel; PILATTE, Isabelle, Noelle, Constance; (157 pag.)WO2018/109088; (2018); 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. 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

Example 274 Synthesis of 5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde To 4-(1H-pyrazol-1-yl)aniline (54 mg, 0.34 mmol), Cs2CO3 (130 mg, 0.4 mmol) were added to tert-butyl 5-chloro-3-formyl-2-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (100 mg, 0.29 mmol) dissolved in 1,4-dioxane (1.1 mL). Racemic BINAP (11 mg, 0.017 mmol) and palladium(II) acetate (8 mg, 0.011 mmol) were then added. The mixture was sealed and irradiated at 110° C. for 60 min in the microwave. Et2O (3 mL) was added and the solution was filtered. The filtrate was concentrated in vacuo. The crude residue was dissolved in dichloromethane (1.5 mL) and trifluoroacetic acid (1.5 mL). After stirring at room temperature for 1 hour, the solution was concentrated under a stream of air. The crude material was purified by silica gel chromatography (15percent acetone/dichloromethane) to yield the product, 5-(4-(1H-pyrazol-1-yl)phenylamino)-7-(cyclopropylamino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carbaldehyde (24 mg, 23percent yield). LCMS (M+1=374)

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; SENHWA BIOSCIENCES, INC.; Haddach, Mustapha; Tran, Joe A.; Pierre, Fabrice; Regan, Collin F.; Raffaele, Nicholas; Ravula, Suchitra; Ryckman, David M.; (417 pag.)US9303033; (2016); B2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 82560-12-1, The chemical industry reduces the impact on the environment during synthesis 82560-12-1, name is 3-Amino-5-tert-butylpyrazole, I believe this compound will play a more active role in future production and life.

Step j04: 3-Tert-butyl-1H-pyrazol-5-amine (J-lll) (1 equivalents, 40 g) was dissolved in diluted HCl (120 mL of HCl in 120 mL of water) and mixed dropwise with NaNO2 (1 .03 equivalents, 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 equivalents, 48 g), water (120 mL) and CuCN (1 .12 equivalents, 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 ethyl acetate (3 x 500 mL), the combined organic phases were dried over sodium sulphate and the solvent was removed under vacuum. The purification (silica gel: 100-200 mesh, eluent: 20 % ethyl acetate/n-hexane) of the residue by column chromatography produced a white solid (J-IV) (6.5 g, 15 %).

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; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68462; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

5334-39-4, name is 3-Methyl-4-nitro-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: 3-Methyl-4-nitro-1H-pyrazole

To a solution of 3-methyl-4-nitro-lH-pyrazole (20 g, 157.36 mmol), cyclopent-3- en-l-ol (15.88 g, 188.83 mmol) and PPh3 (61.91 g, 236.04 mmol) in THF (300 mL) was added D1AD (47.73 g, 236.04 mmol) at 0 C. The mixture was stirred at 25 C for 12 h. The reaction mixture was concentrated under reduced pressure to give a residue, w hich was purified by silica gel chromatography (PE:EtOAc = 50: 1 to 20: 1) to give a mixture of l-(cyclopent-3-en-l-yi)-5-methyl-4-nitro-lH-pyrazoie and 1 -(cyclopent-3-en- 1 -yl)-3-methyl-4-nitro- lH-pyrazole as a yellow oil. LCMS: RT 1.301 min, m/z = 194.1 [M+H].To a mixture of 1-cyclopent- 3-en-l-yl-5-methyl-4-nitro-pyrazole and l-cyciopent-3-en-l-yl-3-methyl-4-nitro-pyrazole (10 g, 51.76 mmol), bis [(Z)-l-methyl-3-oxo-but-l-enoxy]copper (948 mg, 3.62 mmol) in DCE (300 mL) was added a solution of ethyl 2-diazoacetate (23.6 g, 207.04 mmol) in DCE (600 mL) over a period of 12 h at 90 C. The mixture was stirred at 90 C for 4 h. The reaction mixture was concentrated under reduced pressure to give a residue, which was purified by silica gel column chromatography (PE:EtOAc :=: 20: 1 to 5: 1) to give a mixture of ethyl 3-(5-methyl-4-nitro-lH-pyrazol-l-yl)bicyclo[3.1.0]hexane-6-carboxylate and ethyl 3-(3-methy3-4~nitro-lH-pyrazol-l-yl)bicyclo[3.1.0]hexane-6~carboxy as a yellow solid. LCMS: RT 0.831 mm, m/z = 280.1 [M+H]+.

The synthetic route of 5334-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics