Category: 27258-33-9

Application of 27258-33-9, These common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-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.

(l-{4-[5-Amino-2-(3-trifluoromethoxy-phenyl)-pyrimidin-4-yl-amino]- phenyl}-cyclobutyl)-carbamic acid tert-butyl ester (200 mg 0.77 mmol) was dissolved in acetic acid (30 mL), then 2-Methyl-2H-pyrazole-3-carbaldehyde (93.5 mg, 0.85 mmol) and Cu(OAc)2 (140 mg, 0.77 mmol) were added separately. The reaction mixture was stirred at 100 C for 2 h. LC/MS showed there was about 40% desired product (l-{4-[8-(2-Methyl-2H-pyrazol-3-yl)-2-(3- trifluoromethoxy-phenyl)-purin-9-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester in the reaction mixture. Then the solvent was removed by concentration, and the residue was dissolved in ethyl acetate (150 mL). The organic layer was washed with sat. NaHC03 aqueous solution, followed by brine, dried over sodium sulfate, filtered and concentrated to give 150 mg of crude desired product with 80% purity, which was used directly without further purification. LC/MS (ESI+): e/z: 606.2 [M+l]+.

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; SKELTON, Nicholas; GRADL, Stefan; BLAKE, James F.; GRAHAM, James M.; GUNAWARDANA, Indrani W.; HENTEMANN, Martin; MARLOW, Allison L.; TANG, Tony P.; WO2013/78254; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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. category: pyrazoles-derivatives

Step 2: 3-(2-Methyl-2H-pyrazol-3-yl)-acrylonitrile (4): To a stirred solution of 2-methyl-2H-pyrazole-3-carbaldehyde 3 (3.8 g, 0.0345 mol) in toluene (50 mL) was addedcyanomethyl triphenylphosphonium chloride (12.8 g, 0.0389 mol) at room temperature. DBU (1.52 mL, 0.0099 mol) was then added dropwise and heated to reflux for 3 h. After completion of the reaction, the toluene was distilled off completely under vacuum. The resultant crude product was purified on combi flash, with the desired product eluted in 15% EtOAc:Hexane toafford the product (1.1 g, 24.01% yield) as a white solid. ?HNMR(400 MHz, CDC13) oe 7.46-7.45 (d, J 176Hz, 1H), 7.3-7.25 (m, 1H), 6.56 (s, 1H), 5.79-5.75 (d, J= 16.34Hz, 1H), 3.93 (s, 3H). LC-MS (ES, m/z): [M+Hj 134.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27258-33-9, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MILLER, John; BASTOS, Cecilia, M.; MUNOZ, Benito; (155 pag.)WO2017/112853; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 27258-33-9,Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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.

Compound 24; [6-(2-Methyl-2H-pyrazol-3-ylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl]-quinolin-3-yl- amine; [00404] A 1.5 mL vial was charged with a solution of (6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)- quinolin-3-yl-amine (6.0 mg, 0.023 mmol) and 2-methyl-2H-pyrazole-3-carbaldehyde (0.046 mmol) in dimethyl sulfoxide (150 uL, 2.1 mmol). A solution of sodium triacetoxyborohydride (14 mg, 0.068 mmol) and acetic acid (2.6 uL, 0.046 mmol) in dimethyl sulfoxide (150 uL, 2.1 mmol) was added and the mixture stirred at room temperature. Aliquot (3 uL) after 2 h showed complete conversion. The mixtures were purified by reverse-phase HPLC (25-80% ACN in 10 mM Et2NH/H2O) to afford the title compound.

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; DUNCTON, Matthew; O’MAHONY, Donogh, John, Roger; COX, Matthew; WO2010/59610; (2010); 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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Methyl-1H-pyrazole-5-carbaldehyde

Acetic acid (0.4 mL) was added to a solution of 2-methyl-2H-pyrazole-3-carbaldehyde (0.8 g) and 5-bromopyridine-2,3-diamine (1 g) in THF (20 mL) at room temperature. The mixture was stirred overnight at room temperature. The mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, dried over magnesium sulfate, and then concentrated to obtain a residue. Sodium borohydride (300 mg) was added to a solution of the residue in THF (20 mL)/methanol (50 mL) at 0C, and the mixture was stirred for 1 hour. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was sequentially washed with water and a saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to obtain a pale yellow solid as 5-bromo-N3-((1-methyl-1H-pyrazol-5-yl)methyl)pyridine-2,3-diamine (0.38 g). A mixture of the obtained pale yellow solid (300 mg), acetic acid (0.1 mL), DMAP (10 mg), propylphosphonic anhydride (50% in ethyl acetate solution) (0.938 mL), DIPEA (0.464 mL) and THF (10 mL) was stirred under microwave irradiation at 200C for 2 hours. The mixture was purified by NH silica gel column chromatography (methanol/ethyl acetate) to obtain the title compound (188 mg). 1H NMR (300 MHz, DMSO-d6) delta 2.55 (3H, s), 3.81 (3H, s), 5.63 (2H, s), 5.70 (1H, d, J = 1.9 Hz), 7.30 (1H, d, J = 1.9 Hz), 8.24 (1H, d, J = 2.2 Hz), 8.42 (1H, d, J = 2.2 Hz).

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KAWAKITA Youichi; KOJIMA Takuto; NII Noriyuki; ITO Yoshiteru; SAKAUCHI Nobuki; BANNO Hiroshi; LIU Xin; ONO Koji; IMAMURA Keisuke; IMAMURA Shinichi; (165 pag.)EP3450436; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 27258-33-9,Some common heterocyclic compound, 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, molecular formula is C5H6N2O, 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 stirred solution of 2-Methyl- 2H-pyrazole-3-carbaldehyde (1.00 g, 0.0099 mol) in toluene (30 mL) was added Wittig salt (3.37 g, 0.0099 mol) at room temperature. To this resulted suspension was added DBU (1.52 mL, 0.0099 mole) drop wise and heated to reflux for 3 h. After completion of reaction toluene was distilled off completely under vacuum. Resulted crude oily mass was purified on combi flash. Pure Evaporation of solvent afforded compound 2 (0.450 g, 41.32% yield) as White Solid.Analytical data IH NMR (400 MHz, CDC13) delta: 3.93 (s, 3H), 5.75, 5.79 (s, s, IH total), 6.56- 6.57 (d, IH), 7.26, 7.30 (s, s, IH total), 7.46-7.47 (d, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazole-5-carbaldehyde, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; TAIT, Bradley; CULLEN, Matthew; WO2014/210159; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 27258-33-9, 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 27258-33-9 as follows.

To a solution of 1 -methyl- lH-pyrazole-5-carbaldehyde (1.0 g, 9.09 mmol) in DMF (8 mL) was slowly added NBS (1.62 g, 9.09 mmol) in DMF (5 mL). The mixture was stirred for overnight at room temperature. 1 N NaOH (9.1 mL) was added and the solution was stirred for 10 min, diluted with water (100 mL), extracted with EtOAc (30 mL* 3), dried over MgS04, filtered and concentrated to afford an orange solid (1.57 g, 92%). LRMS m/z (M+H) 187.9 found, 188.0 required.

According to the analysis of related databases, 27258-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey, C.; KUDUK, Scott, D.; REGER, Thomas, S.; WO2014/81619; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, 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. Safety of 1-Methyl-1H-pyrazole-5-carbaldehyde

General procedure: A mixture of the corresponding secondary phosphinechalcogenide1 (1.00 mmol) and carbaldehyde2 or 4 (1.05 mmol) in toluene(2 ml) was stirred at 23-50 C for 6 to 94 h in argon atmosphere (seeOnline Supplementary Materials for details). Toluene was removed undervacuum, and the residue was washed with Et2O (1 ml), dissolved in CHCl3and re-preciptatedwith n-hexane. The resulting solid was collected, driedunder vacuum to afford alcohols 3 or 5.

The synthetic route of 27258-33-9 has been constantly updated, and we look forward to future research findings.

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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., COA of Formula: C5H6N2O

S3, the step S2 product 1-methyl-1H-pyrazole-5-carbaldehyde 130g was added to 1100ml of pyridine,An additional 10 ml of piperidine,140g malonic acid,Then warmed to 70 degrees Celsius, the reaction 0.5h,Then keep the temperature reflux 3h,After the cooling step, all the pyridine was evaporated under reduced pressure, 200 ml of ethanol was added,Precipitated solid, the precipitated solid was suction filtered and dried,The product of S3 step 3- (1-methyl-1H-pyrazol-5-yl) acrylic acid was obtained as a solid at room temperature.

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.

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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde, A new synthetic method of this compound is introduced below., Formula: C5H6N2O

To a solution of triethyl phosphonoacetate (26.9 g) in tetrahydrofuran (200 ml) was added sodium hydride (60% dispersion in mineral oil, 4.8 G) by portions under ice- cooling. The mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added 1-METHYL-LH-PYRAZOLE- 5-carbaldehyde (33.0 g) in tetrahydrofuran (165 ml) at room temperature, and the mixture was stirred at the same temperature for 1.5 hours. To the resulting solution was added 10% aqueous potassium hydrogen sulfate solution. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with saturated sodium hydrogen carbonate solution and brine. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give ethyl (2E)-3-(1-METHYL-LH-PYRAZOL-5-YL)-2-PROPENOATE (33.4 g) as an oil. IR (neat) 2981,2943, 1713,1703, 1180,781 CM~1. H-NMR (DMSO-d6) 8 1. 26 (3H, t, J = 7.1 Hz), 3.88 (3H, s), 4.20 (2H, q, JAZZ 7.1 Hz), 6.54 (1H, d, J = 15.8 Hz), 6.88 (1H, d, J = 1.8 Hz), 7.45 (1H, d, J = 1.8 Hz), 7.60 (1H, d, J = 15.8 Hz). MS (APCI) 181 (M+H+).

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.

Related Products of 27258-33-9, 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. 27258-33-9, name is 1-Methyl-1H-pyrazole-5-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of aluminum lithium hydride (691 mg) in THF (10 ml), a solution of 1-methylpyrazole-5-carboxyaldehyde (2.0 g) in THF (20 ml) was added dropwise at 0C under nitrogen atmosphere. After finishing the dropping, water (0.7 ml), 15% aqueous solution of sodium hydroxide (0.7 ml) and water (2.1 ml) were sequentially added to the mixture at 0C, and the mixture was stirred for 2 hours at room temperature. The mixture was dried over magnesium sulfate, and the insolubles were filtered off. The solvent was distilled off under reduced pressure, to give 5-hydroxymethyl-1-methylpyrazole (2.04 g) as colorless oil. 1H-NMR (200 MHz, CDCl3) delta 3.90 (3H, s), 4.68 (2H, s), 6.19 (1H, d, J = 2.0 Hz), 6.39 (1H, d, J = 1.8 Hz)

The synthetic route of 1-Methyl-1H-pyrazole-5-carbaldehyde has been constantly updated, and we look forward to future research findings.