Category: 5334-39-4

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-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 5334-39-4, Quality Control of 3-Methyl-4-nitro-1H-pyrazole

A mixture of 3-methyl-4-nitro-lH-pyrazole ( 5 g, 39.34 rnmol), 2-bromoethanoi (9.83 g,78.68 mmol, 5.59 mL) and K2CO3 (16.31 g, 118.02 mmol) in CCN (50 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80 C for 16 h under N2. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was poured into ice water (100 mL). The aqueous phase was extracted with EtOAc (3 chi 35 mL). The combined organic phase was washed with brine (35 mL), dried over anhydrous NaaSC^, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give 2-(5-methyl-4-nitro-pyrazol- 1 -yl)ethanol and 2-(3-methyl-4-nitro-pyrazol-1-yl)ethanol as a yellow oil. LCMS: RT 0.161 min, m/z = 172.2 [M+H]~. -1 NMR (400 MHz, CDC13): delta 8.20 (s, 1 H), 8.03 (s, 1 H), 4.14 – 4.22 (rn, 4 H), 3.94 – 4.03 (m, 4 H), 3.07 (d, 1=5.27 Hz, 2 H), 2.64 (s, 3 H), 2.47 (s, 3 H).To a solution of 2-(5-methyl-4-nitro-pyrazol-l-yl)ethanol (19-2, 4.26 g, 24.89 mmol,), 2-(3-methyl-4-nitro-pyrazol-l-yl)ethanol and Cul (948 mg, 4.98 mmol,) in CH3CN (100 mL) was added a solution of 2,2-difluoro-2-fiuorosulfonyl-acetic acid (6.65 g, 37.34 mmol, 3.87 mL) in CH3CN (10 mL) dropwise at 55 C over a period of 30 min under N2. The reaction mixture was stirred at 55 C for another 2 h. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1 ), to give a mixture of l-[2- (difluoromethoxy)ethyl] -5 -methyl -4-nitro-pyrazole and 1 – [2-(difiuoromethoxy)ethyl -3 -methyl -4-nitro- pyrazole as a yellow oil. LCMS: RT 0.707 min, m/z = 222.1 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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

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 5334-39-4 as follows. Formula: C4H5N3O2

(a) tert-Butyl 3-methyl-4-nitro- 1H-pyrazole- 1-carboxylate or tert-butyl 5-methyl-4- nitro- 1H-pyrazole- 1-carboxylate (A25)Di-tert-butyl dicarbonate (5.15 g, 23.6 mmol) and 4-dimethylaminopyridine (0.481 g, 3.93 mmol) were added to a solution of 3-methyl-4-nitropyrazole (2.50 g, 19.7 mmol)in DCM (100 mL) and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed with water (100 mL), brine (100 mL), dried (phase separator) and concentrated under reduced pressure. The residue was adsorbed onto Si02 and purified by column chromatography (Biotage Isolera, 2 x 40 g Si02 cartridges, 0-50% EtOAc in petroleum benzine 40-60 00) to give the title compoundA25 as a white solid (2.54 g, 57%). LCMS-D: rt 3.39 mm; no product ion detected.

According to the analysis of related databases, 5334-39-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; FOITZIK, Richard Charles; MORROW, Benjamin Joseph; HEMLEY, Catherine Fae; LUNNISS, Gillian Elizabeth; CAMERINO, Michelle Ang; GANAME, Danny; STUPPLE, Paul Anthony; LESSENE, Romina; KERSTEN, Wilhelmus Johannes Antonius; HARVEY, Andrew John; HOLMES, Ian Peter; WO2014/26243; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 5334-39-4, name is 3-Methyl-4-nitro-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 5334-39-4, Recommanded Product: 5334-39-4

To a solution of 3 -methyl -4-nitro-lH-pyrazole (5 g, 39.34 mmol) in DMF (50 rnL) was added NaH (1.89 g, 47.21 mmol, 60% purity) at 0 C under N2. The mixture was stirred at 20 C for 1 h, then added with ethyl 2-chloropropanoate (10.75 g, 78.68 mmol, 10.05 mL) and stirred for 15 h. The mixture was poured into ice water (250 mL). The aqueous phase was extracted with EtOAc (3 chi 100 mL). The combined organic phase was washed with brine (3 chi 100 mL), dried over anhydrous NaaS&t, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give a mixture of ethyl 2-(5-methyi-4-nitro-pyrazoi-l-yl)propanoate and ethyl 2-(3- methyl-4-nitro-pyrazol-l-yl)propanoate as a yellow oil LCMS: RT 0.745 min, m/z = 228.2 [M+H]+ To a mixture of ethyl 2-(5-methyl-4-nitro-pyrazol-l -yl)propanoate and ethyl 2-(3-methyl-4-nitro- pyrazol-l-yl)propanoate (9.3 g, 40.93 mmol) in MeOH (90 mL) was added NaBH4 (3.87 g, 102.33 mmol) at 0 C under N2. The mixture was stirred at 0 C for 2 h. The mixture was concentrated under reduced pressure and purified by silica gel column chromatography (PE:EtOAc = 3: 1), to give a mixture of 2-(5- methyl-4-nitro-pyrazol- l-yl)propan-l -ol and 2-(3-methyl-4-nitro-pyrazol-l-y])propan-l-ol was obtained as a yellow solid. LCMS: RT 0.707 mm, m/z = 222.1 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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

Synthetic Route of 5334-39-4, 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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-methyl-4-nitro-lH-pyrazole (5 g, 39.34 mmol) and tetrahydropyran-4-ol (4.82 g, 47.21 mmol, 4.73 mL) in THF (70 mL) was added PI3 (15.48 g, 59.01 mmol) and DIAD (11.93 g, 59.01 mmol . 1.47 mL) in one portion at 0C under N2. The mixture was stirred at 0 C for 60 min, then warmed to 25 C and stirred for 16 h. The mixture was poured into the mixture of PE and EtOAc (PE:Ei()Ac = 1 : 1) (100 mL), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 5: 1) to afford 5- methyl-4-iiitro-l-tetrahydropyran-4-yl-pyrazole and 3-methyl-4-nitro~l -tetrahydro-2H~pyran~4-yl~ pyrazole as yellow solids. LCMS: RT 0.610 min, m/z = 212.2 [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, 3-Methyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

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

Reference of 5334-39-4, These common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-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.

To a solution of 3 -methyl ~4-nitro- lH-pyrazole ( 10 g, 78,68 mmol) in DMF (50 mL) was added portionwise NaH (4.72 g, 1 18 ,02 mmol, 60% purity) at 0 C over 30 min. After addition, the mixture was stirred at 20 C for 30 min, and then 3- bromo-3-methylbutan-2-one ( 15.58 g, 94.42 mmol) was added dropwise at 0 C. The resulting mixture was stirred at 20 C for 1 1 h. The reaction mixture was quenched by addition of H20 (250 mL) at 0C, and extracted with EtOAc (3 chi 100 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO/j, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (PE/EtOAc = 20/1 to 3/1). 3-methyl-3-(3-methyi-4- nitro-lH-pyrazol-l-yl)butan-2-one was obtained as a yellow solid. LCMS: RT 0.674 min, m/z = 212 [M + H]+. ‘H NMR (400 MHz, CDC13): 6 ppm 8.30 (s, 1 H) 2.56 (s, 3 H) 1.98 (s, 3 H) 1.75 (s, 6 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

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

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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole, A new synthetic method of this compound is introduced below., SDS of cas: 5334-39-4

A mixture of 3-methyl-4-nitro-lH-pyrazole (1.36 g, 10.71 mmol), tert-butyl-4- iodopiperidine-l-carboxylate (10.00 g, 32.14 mmol) and K2CO3 (2.96 g, 21.42 mmol) in DMF (16.6 mL) was stirred at reflux for 24 h. The reaction mixture was diluted with EtOAc and water and the layers were separated. The organic layer was washed with brine, dried over MgS04, filtered and was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (irregular SiOH 40 muiotaeta, 80 g, mobile phase: heptane/DCM, gradient from 50:50 to 0: 100). The pure fractions were combined and the solvent was evaporated to give a mixture of intermediate 349 and intermediate 349′ (540.00 mg, 16% yield). intermediate 350 intermediate 350′ At 0C, HC1 (4M in dioxane) (15.00 mL, 60.00 mmol) was added to a solution of a mixture of intermediates 349 and 349′ (0.54 g, 1.74 mmol) in 1,4-dioxane (4 mL). The reaction was stirred at rt overnight. The solvent was evaporated until dryness. The residue was taken up into DCM and basified with a 10% aqueous solution of K2C03. The organic layer was dried over MgS04, filtered and the solvent was evaporated until dryness. The residue (817 mg) was purified by column chromatography on silica gel (stationary phase: irregular SiOH, 15-40 muiotaeta, 40 g, mobile phase: 98% DCM, 2% MeOH (+ 10% NH4OH) to 95% DCM, 5% MeOH (+10% NH4OH)). The pure fractions were collected and the solvent was evaporated until dryness to give 0.480 g of a mixture of intermediates 350 and 350′ used as it for the next step.

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.

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. 5334-39-4, name is 3-Methyl-4-nitro-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-Methyl-4-nitro-1H-pyrazole

A mixture of 3-methyl-4-nitro-lH-pyrazole ( 5 g, 39.34 rnmol), 2-bromoethanoi (9.83 g,78.68 mmol, 5.59 mL) and K2CO3 (16.31 g, 118.02 mmol) in CCN (50 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 80 C for 16 h under N2. The mixture was cooled to 20 C and concentrated under reduced pressure. The residue was poured into ice water (100 mL). The aqueous phase was extracted with EtOAc (3 chi 35 mL). The combined organic phase was washed with brine (35 mL), dried over anhydrous NaaSC^, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE:EtOAc = 2: 1), to give 2-(5-methyl-4-nitro-pyrazol- 1 -yl)ethanol and 2-(3-methyl-4-nitro-pyrazol-1-yl)ethanol as a yellow oil. LCMS: RT 0.161 min, m/z = 172.2 [M+H]~. -1 NMR (400 MHz, CDC13): delta 8.20 (s, 1 H), 8.03 (s, 1 H), 4.14 – 4.22 (rn, 4 H), 3.94 – 4.03 (m, 4 H), 3.07 (d, 1=5.27 Hz, 2 H), 2.64 (s, 3 H), 2.47 (s, 3 H).

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

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: 5334-39-4

To a solution of 3-methyl-4-nitro-lH-pyrazole (1 -1, 398 nig, 3.13 mmol) in DMF (10 niL) was added NaH (125 mg, 3.13 mmol, 60% purity) at 0 C, then the reaction was stirred at 20 C for 1 h. Then, (3-methyl- 5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridin-6-yl) methanesulfonate (604 mg, 2.61 mmol, 70% purity) in DMF (4 mL) was added to the solution at 20 C. Then, the mixture was stirred at 80 C for 12 h. The reaction solution was added with NH4Q solution (20 ml,), extracted with DCM:MeOH (20 mL chi 3, ratio=3: l). The organic layers were combined, dried over Na2S04, filtered and concentrated under reduced pressure. The crude product was purified by prep-TLC (DCM:MeOH = 5: 1) to give a mixture of 3-niethy3~6~(3-methyi-4~nitro^ and 3- methyl-6-(5~methyl-4-nitro-pyra^ as a yellow gum. LCMS: RT 0.925 min, m/z = 263.1 | M – H j ‘ . NMR (400 MHz, CDC13): delta 8.25 (s, 0.6 H), 8.13 (s, 0.3 H), 4.68 – 4.81 (m, 1 H), 4.14 – 4.42 (m, 2 H), 3.02 – 3.31 (m, 2 H), 2.77 (s, 1 H), 2.55 (s, 2 H), 2.44 – 2.53 (m, 4 H), 2.43 (s, 1 1H 1).To a mixture of 3-methyl-6-(3-methyl-4-nitro-pyrazol-l-yl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-aJpyri and 3-me1hyl-6-(5-methyl-4-nitro-pyrazol-l-yl)-5,6,7,8-tetrahydro-[l ,2,4]triazolo[4,3-a]pyridm (100 mg, 381.29 muetaiotaomicron) in Me OH (10 mL) was added Pd/C (10%, 50 mg) under N2. The suspension was degassed and purged with H2 for 3 times. The mixture was stirred under H2 ( 15 psi) at 20 C for 5 h. The reaction solution was filtered through a pad of celite, the filtrate was concentrated under reduced pressure to give a crude 5 -methyl- 1 -(3 -methyl-5 ,6,7,8 -tetrahydro- j 1 ,2,4 jtriazolo [4,3 -a]pyridin-6-yl)pyrazol-4-amine and 3 – m.ethyi~-(3-ni6thyl~5,6,7,8~tetrahy LCMS: RT0.173 min, m/z = 233.1 [M+H]+.

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

Related Products of 5334-39-4, These common heterocyclic compound, 5334-39-4, name is 3-Methyl-4-nitro-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.

To a solution of PPh3 (20.64 g, 78.68 mmol) in THF (30 rnL) was added DIAD ( 15.91 g, 78.68 mmol, 15.30 mL), 3 -methyl -4-nitro- lH-pyrazole (5 g, 39.34 mmol) and oxetan-3-ol (2.91 g, 39.34 mmol) at 0C. Then the mixture was stirred at 25C for 12 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (S1Q2, PE:EtOAc = 50: 1 to 5 : 1). The mixture of 3-methy]-4-nitro-l -(oxetan-3-yl)pyrazole and 5 -methyl -4-nitro- 1 -(oxetan-3-yl)pyrazole was obtained as a yellow solid. To a solution of Pd/C (3 g, 10% purity) in MeOH (lOmL) was added 3 -methyl -4-nitro- l-(oxetan-3- yl)pyrazole and 5-methyl-4-nitro-l-(oxetan-3-yl)pyrazole (5 g, 37,3 mmol), then the mixture was stirred at 25C under (15 psi) for 2 h. The reaction was filtered and the filtrate was concentrated under reduced pressure to give 3 -methyl- l-(oxetan-3-yl)pyrazol-4-amine and 5-methyl- l-(oxetan-3-yl)-pyrazol- -I -am ine as a dark brown oil.

Statistics shows that 3-Methyl-4-nitro-1H-pyrazole is playing an increasingly important role. we look forward to future research findings about 5334-39-4.