Category: 25016-12-0

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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

General procedure: Sodium triacetoxyborohydride (46.3 mg, 0.218 mmol) was added toa mixture of 10c (65 mg, 0.146 mmol) and tetrahydropyran-4-carbaldehyde(18.3 mg, 0.160 mmol) in 1,2-dichloroethane (1.30 mL). The mixture was stirred at room temperature for 2 h, sat.NaHCO3 aqueoussolution was added, and the mixture was extracted with CHCl3. The organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CHCl3/MeOH) to give the desired compound as a white solid (41.0 mg, 52%). 1H NMR (DMSO-d6) delta1.00-1.29 (3H, m), 1.44-1.60 (3H, m), 1.64-1.85 (3H, m), 1.95-2.17(5H, m), 2.62-2.71 (1H, m), 2.78-2.88 (1H, m), 3.08 (3H, s), 3.15-3.29(2H, m), 3.70-3.83 (2H, m), 4.01 (3H, s), 4.05 (3H, s), 4.27-4.37 (2H,m), 7.26 (1H, s), 8.11 (1H, s), 8.43 (1H, d, J=2.3 Hz), 8.85 (1H, d,J=2.3 Hz), 9.37 (1H, s); ESI-MS m/z 545.3 [(M+H)+]; HRMS(ESI) m/z calcd for C26H37N6O5S [(M+H)+]: 545.2541, found: 545.2537

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hamajima, Toshihiro; Takahashi, Fumie; Kato, Koji; Sugano, Yukihito; Yamaki, Susumu; Moritomo, Ayako; Kubo, Satoshi; Nakamura, Koji; Yamagami, Kaoru; Hamakawa, Nozomu; Yokoo, Koji; Fukahori, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3917 – 3924;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 25016-12-0,Some common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H8N2O, 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: To a solution of Example 13 (53 mg, 0.17 mmol, 1.0 eq) and 1-methyl-1H-imidazole-2-carbaldehyde (28 mg, 0.25 mmol, 1.5 eq) in THF (2 mL) under a N2 atmosphere was added NaBH(OAc)3 (72 mg, 0.34 mmol, 2.0 eq) and the mixture was stirred at RT overnight. The mixture was purified by C18 reverse phase column (Biotage, 30% to 70% ACN in water, 0.1% TFA) to afford the title compound (22 mg, 34%) as a white solid. LCMS: [M+H]+ 384.2. 1H NMR (400 MHz, CDCl3) delta 8.10 (d, J=8.4 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 7.41 (s, 2H), 7.20 (s, 1H), 4.78 (s, 2H), 3.98 (s, 3H), 3.80 (s, 2H), 3.40 (m, 2H), 3.17-3.00 (m, 3H), 2.59 (s, 3H), 2.24 (m, 2H), 1.95 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Ribon Therapeutics Inc.; Schenkel, Laurie B.; Vasbinder, Melissa Marie; Kuntz, Kevin Wayne; Swinger, Kerren Kalai; (179 pag.)US2019/194174; (2019); 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C6H8N2O

To a solution of l,3-dimethyl-li/-pyrazole-4-carbaldehyde (1.00 g, 8.06 mmol) in nitromethane (35 mL) was added ammonium acetate (0.155 g, 2.01 mmol). The reaction mixture was heated at reflux overnight. Excess nitromethane was removed under reduced pressure. The residue was purified by automated flash silica column chromatography (40 g column) eluting with a gradient of 20-50% EtOAc in heptanes. The fractions were evaporated to give the title compound as a yellow solid (1.31 g, 97%). ESI-MS [M+H]+ calc?d for C7H9N3O2, 168.08; found, 168.2.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; GREEN, Jason; JOHNSON, Ben; SCHLEICHER, Kristin; SUN, Huikai; TANG, Mingnam; (257 pag.)WO2019/169153; (2019); 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

To a suspension of tert-butyl 5-((2-amino-5-chloro-3-nitropyridin-4- yl)amino)hexahydrocyclo- penta[c]pyrrole-2(lH)-carboxylate (0.62 g, 1.60 mmol) and 1,3- dimethylpyrazole-4-carbaldehyde (0.22 g, 1.78 mmol) in EtOH (30.0 mL) was added a freshly prepared aqueous solution of sodium dithionite (6.30 mL, 6.30 mmol, 1.0 mol/L). The mixture was heated at 85 C overnight. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v) = 50/1 to 30/1 to 20/1) to afford the title compound as a white solid (0.50g, yield 68%).MS (ESI, pos. ion) m/z: 472.3 [M+H]+; MR (600 MHz, CDC ) delta (ppm): 7.87 (s, 1H), 7.72 (s, 1H), 5.49 – 5.39 (m, 1H), 5.03 (d, J = 8.4 Hz, 1H), 3.92 (s, 3H), 3.58 – 3.48 (m, 2H), 3.46 – 3.33 (m, 2H), 2.80 – 2.72 (m, 2H), 2.69 – 2.60 (m, 5H), 1.50 (s, 9H), 1.48 – 1.40 (m, 2H).

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; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Xiaobo; LI, Mingxiong; ZHANG, Tao; HU, Haiyang; WU, Yanjun; (139 pag.)WO2018/169700; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, 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 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde

To a solution of 4-(4-((1 ,2,4-oxadiazol-3-yl)methyl)piperazin-1 -yl)-5-chloro-3- nitropyridin-2-amine (50.0 mg, 0.147 mmol) and 1 ,3-dimethyl-1 /-/-pyrazole-4- carbaldehyde (19.2 mg, 0.155 mmol) in EtOH (3.4 mL) was added 1 M Na2S204 (0.588 mL, 0.588 mmol, freshly prepared) and the solution was heated to 80 C and stirred for 15 h whilst being open to air. Once cooled, the reaction was evaporated in vacuo and the residue dry loaded onto silica. Purification was accomplished by flash chromatography on silica gel (2 x 14) eluting with MeOH/CH2CI2 (5-7.5%) to yield the title compound (26 mg, 43%) as a pale yellow solid. [00129] 1 H-NMR (500 MHz, CDCI3) 2.58 (s, 3H, CH3), 2.81 (app t, J = 4.4 Hz, 4H, CH2), 3.82 (app s, 4H, CH2), 3.85 (s, 3H, NCH3), 3.88 (s, 2H, -CH2-), 7.62 (br s, 1 H, CHar), 7.87 (br s, 1 H, CHar), 8.74 (s, 1 H, CHar), 13.04 (s, 1 H, NH); [00130] LC – MS (ESI, m/z): Rt = 1 .91 min – 414, 416 [(M + H)+, CI isotopic pattern]; [00131] HRMS: Found: 436.1374, calculated for C18H20N9OCINa (M+Na)+: 436.1372.

The synthetic route of 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190319; (2013); 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 25016-12-0 as follows. Recommanded Product: 25016-12-0

General procedure: Aldehyde (1.0 equiv) is a dissolved in anhydrous methanol (0.2-0.5 mM) and charged with cesium carbonate (1.0 equiv) and cooled to 0-5 oC . Dimethyl (1-diazo-2-oxopropyl)phosphonate (1.0 equiv) is added dropwise after which the reaction is allowed to stir for 1-18h after which the crude mixture is concentrated onto silica gel and purified directly by flash silica gel chromatography to provide the desired alkyne J-1.

According to the analysis of related databases, 25016-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; EVANS, Catherine, A.; TREMBLAY, Martin, R.; (288 pag.)WO2016/54491; (2016); 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C6H8N2O

In a sealed tube, under N2, 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (284 mg; 2.28mmol) and Ti(iPrO)4 (727 jiL; 3.05 mmol) were added to a solution of intermediate 11(500 mg; 1.52 mmol) in THF (10 mL). The solution was stirred at 50C for 2h. Thereaction mixture was cooled to 5C and iPrMgCl (3.8 mL; 7.61 mmol) was addeddropwise. The reaction mixture was allowed to rise slowly to rt and stirred overnight. The reaction mixture was poured onto a 10% aqueous solution of K2C03 and EtOAc. The insoluble was filtered through a pad of celite then, the organic layer was decanted, dried over MgSO4, filtered and the solvent was evaporated. The residue (866 mg, brownoil) was purified by chromatography over silica gel (Si02 40 g; eluent: from 96% DCM,4% MeOH, 0.4% NH4OH to 93% DCM, 7% MeOH, 0.7% NH4OH). The pure fractionswere collected and the solvent was evaporated to dryness. The residue (496 mg, yellow oil) was recrystallized with diethylether. The precipitate was filtered and dried to give324 mg of compound 161( (45%, white solid).

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; PANDE, Vineet; HERKERT, Barbara; KROSKY, Daniel, Jason; QUEROLLE, Olivier, Alexis, Georges; PILATTE, Isabelle, Noelle, Constance; PATRICK, Aaron, Nathaniel; (250 pag.)WO2018/50686; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 25016-12-0, 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0242] Bis(2-methoxyethyl)aminosulfurtrifluoride (3.71 ml, 20.14 mmol)was added to a stirred solution of l,3-dimethyl-lH-pyrazole-4-carbaldehyde (500 mg, 4.03 mmol) in DCM (6 ml) at 0 C. Then the mixture was stirred at room temperature for overnight. The reaction was quenched by NaHC03 solution (20 ml), extracted with dichloromethane (3 x lOmL). The combined organic fractions were washed with brine (3 x 10 ml), dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC reverse phase (C-8), eluting with (MeCN/H20=2/l), to give 4-(difluoromethyl)-l,3-dimethyl-lH- pyrazole as an oil. LC/MS = 147 [M+l].

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, 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUANG, Rongze; TING, Pauline; ALI, Amjad; WU, Heping; BERLIN, Michael; STAMFORD, Andrew; WANG, Hongwu; ZHOU, Gang; KIM, David; DENG, Qiaolin; LIM, Yeon-Hee; YU, Younong; (201 pag.)WO2016/81290; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 25016-12-0, A common heterocyclic compound, 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde, molecular formula is C6H8N2O, 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.

[00120] To a mixture of 5-chloro-4-(4-(4-chlorobenzyl)piperazin-1 -yl)-3-nitropyridin-2- amine (0.076 g, 0.20 mmol) and EtOH (4.0 ml.) was added 1 ,3-dimethyl-1 H-pyrazole-4- carbaldehyde (0.027 g, 0.22 mmol) followed by a freshly prepared aqueous solution of Na2S204 (1 M; 0.85 ml_, 0.85 mmol). The reaction mixture was stirred at 80 C for 24 h, it was then allowed to cool to room temperature, concentrated in vacuo, and the residue was absorbed on silica gel and placed on a 10 g isolute silica column. Elution with ethyl acetate / dichloromethane (v/v; 1 :1 ), and then 4% methanol in ethyl acetate / dichloromethane (v/v; 1 :1 ) afforded the title compound as a white solid after trituration with diethyl ether (0.023 g, 25%).

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BLAGG, Julian; BAVETSIAS, Vassilios; MOORE, Andrew S.; LINARDOPOULOS, Spyridon; WO2013/190319; (2013); A1;,
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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H8N2O

General procedure: Sodium triacetoxyborohydride (46.3 mg, 0.218 mmol) was added toa mixture of 10c (65 mg, 0.146 mmol) and tetrahydropyran-4-carbaldehyde(18.3 mg, 0.160 mmol) in 1,2-dichloroethane (1.30 mL). The mixture was stirred at room temperature for 2 h, sat.NaHCO3 aqueoussolution was added, and the mixture was extracted with CHCl3. The organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CHCl3/MeOH) to give the desired compound as a white solid (41.0 mg, 52%). 1H NMR (DMSO-d6) delta1.00-1.29 (3H, m), 1.44-1.60 (3H, m), 1.64-1.85 (3H, m), 1.95-2.17(5H, m), 2.62-2.71 (1H, m), 2.78-2.88 (1H, m), 3.08 (3H, s), 3.15-3.29(2H, m), 3.70-3.83 (2H, m), 4.01 (3H, s), 4.05 (3H, s), 4.27-4.37 (2H,m), 7.26 (1H, s), 8.11 (1H, s), 8.43 (1H, d, J=2.3 Hz), 8.85 (1H, d,J=2.3 Hz), 9.37 (1H, s); ESI-MS m/z 545.3 [(M+H)+]; HRMS(ESI) m/z calcd for C26H37N6O5S [(M+H)+]: 545.2541, found: 545.2537

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hamajima, Toshihiro; Takahashi, Fumie; Kato, Koji; Sugano, Yukihito; Yamaki, Susumu; Moritomo, Ayako; Kubo, Satoshi; Nakamura, Koji; Yamagami, Kaoru; Hamakawa, Nozomu; Yokoo, Koji; Fukahori, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3917 – 3924;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics