Category: 51105-90-9

Related Products of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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. Methyl 1 /-/-pyrazole-4-carboxylate was reacted with cyclopropylboronic acid and copper(ll) acetate to generate methyl 1 -cyclopropyl-1 /-/-pyrazole-4-carboxylate, which was hydrolyzed with lithium hydroxide to afford 1 -cyclopropyl-1 /-/-pyrazole-4- carboxylic acid.

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

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; BECK, Elizabeth Mary; BUTLER, Christopher Ryan; ZHANG, Lei; O’NEILL, Brian Thomas; BARREIRO, Gabriela; LACHAPELLE, Erik Alphie; ROGERS, Bruce Nelsen; WO2015/155626; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

Step 1: Preparation of Methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate To a solution of methyl 1H-pyrazole-4-carboxylate (0.3 g, 2.4 mmol) and DBU (0.39 mL, 2.6 mmol) in acetonitrile (12 mL) was slowly added dimethylsulfamoyl chloride (0.27 mL, 2.51 mmol). The reaction mixture was stirred at rt for 1 h and was then concentrated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic phase was washed with 10% citric acid, water, and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel chromatography eluting with a gradient of 5% ethyl acetate in DCM, to provide methyl 1-(N,N-dimethylsulfamoyl)-1H-pyrazole-4-carboxylate (0.54 g), LCMS-ESI (POS.) m/z 310.0 (M+H)+.

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

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 51105-90-9,Some common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, molecular formula is C5H6N2O2, 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.

DIAD (9.39 ml, 43.61 mmol) was added dropwise to an ice-cooled solution of methyl 1 H-pyrazole-4- carboxylate (5 g, 39.65 mmol), tert-butyl (2-hydroxyethyl)carbamate (6.13 ml, 39.65 mmol) and PPrtj (1 1 .44 g, 43.61 mmol) in THF (300 ml). The reaction was then allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenchedwith water (150 ml) and the layers separated. The aqueous layer was extracted using EtOAc (3 x 150 ml). The combined organic layers were washed with brine, dried (MgS04), filtered and the solvent evaporated to give the crude product. Purification by flasn column chromatography (eluting with a gradient of 15-100% EtOAc / heptane) gave the title compound (1 1 .3 g, 68%) as a white solid. 1 H-NMR (CDCI3, 500 MHz): d[ppm]= 7.93 (s, 1 H), 7.87 (s, 1 H), 4.25 (t, J = 5.3 Hz, 2H), 3.83 (s, 3H), 3.61- 3.54 (m, 2H), 1.44 (s, 9H) HPLCMS (Method A): [m/z]: 270.1 [M+Hf

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

Reference:
Patent; VIFOR (INTERNATIONAL) AG; DUeRRENBERGER, Franz; BUHR, Wilm; BURCKHARDT, Susanna; BURGERT, Michael; KALOGERAKIS, Aris; REIM, Stefan; MANOLOVA, Vania; BOYCE, Susan; YARNOLD, Christopher John; PENA, Paula; SHEPHERD, Jon; LECCI, Cristina; JARJES-PIKE, Richard; SCOTT, John; (416 pag.)WO2017/68089; (2017); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, 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. SDS of cas: 51105-90-9

. A solution of methyl 1H-pyrazole-4-carboxylate (500 mg, 3.97 mmol) and dry THF (10 mL) was added to a 0 C (ice/water) suspension of sodium hydride in mineral oil (317 mg, 60% purity,7.93 mmol) and dry THF (10 mL) and was stirred for 1 h with gradual warming to 10 C. The reaction was then treated with a solution of SEM-Cl (793 mg, 4.76 mmol) and dry THF (5 mL) at 0 C and was stirred overnight at 10 C. The reaction was quenched with saturated aqueous NH4C1 (20 mL) and concentrated to dryness. The aqueous phase was extracted with ethyl acetate (20 mL x 2), dried over anhydrous Na2504, filtered, and concentrated to dryness. Theresidue was purified by flash column chromatography (gradient eluent: petroleum ether: ethyl acetate = 100:0 to 85:15) to provide the title compound (400 mg, 39% yield) as a colorless oil. MS (ESI): mass calcd. for C11H20N2O3Si, 256.12; m/z found, 256.9 [M+H]t ?HNMR (400IVIHz, CDC13): oe 8.06 (s, 1H), 7.94 (s, 1H), 5.43 (s, 2H), 3.84 (s, 3H), 3.57 (t, J 8.0 Hz, 2H), 0.91 (t, J= 8.0 Hz, 2H), -0.02 (s, 9H).

The synthetic route of 51105-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BACANI, Genesis M.; CHAI, Wenying; KOUDRIAKOVA, Tatiana; KRAWCZUK, Paul J.; KREUTTER, Kevin D.; LEONARD, Kristi; RIZZOLIO, Michele C.; SEIERSTAD, Mark; SMITH, Russel C.; TICHENOR, Mark S.; VENABLE, Jennifer D.; WANG, Aihua; (452 pag.)WO2018/112382; (2018); 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 51105-90-9 as follows. Formula: C5H6N2O2

General procedure: Sulfonamide A (e.g.1.29 mmol) was dissolved in acetonitrile (15 mL in case of 1.29 mmol scale) and finely powdered potassium carbonate (3.0 eq) and the corresponding azole(1.5 eq) were added. Stirring was continued at 100 – 110C until TLC showed consumption of starting material. The solvent was removed under reduced pressure, followed by addition of water and dichloromethane. Afterwards, the phases were separated, the organic phase was dried and it was concentrated in vacuo. The crude was either used without further purification or purified as indicated in the examples.

According to the analysis of related databases, 51105-90-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; CLEVE, Arwed; BRAeUER, Nico; HERBERT, Simon, Anthony; KOCH, Markus; DAHLLOeF, Henrik; OSMERS, Maren; HARDAKER, Elizabeth; LISHCHYNSKYI, Anton; (673 pag.)WO2017/191000; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 51105-90-9, These common heterocyclic compound, 51105-90-9, name is Methyl 1H-pyrazole-4-carboxylate, 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.

Synthesis of methyl 1-((6-cyclopropyl-8-(3-hydroxyoxetan-3-yl)imidazo[1,2-a]pyridin-2-yl)methyl) -1H-pyrazole-4-carboxylate. A mixture of 3-(2-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridin-8-yl)oxetan-3-ol (1.2 g, 4.3 mmol), methyl 1H-pyrazole-4-carboxylate (0.54 g, 4.3 mmol) and Cs2CO3 (2.8 g, 8.6 mmol) in DMF (10 mL) was stirred at 50 C. for 3 h. The reaction mixture was filtered through celite, and the filtrate was diluted with H2O (100 mL) and extracted with ethyl acetate (100 mL). The combined organic layers were concentrated to give the crude, which was purified by silica gel column chromatography (DCM/MeOH=6/1) to give methyl 1-((6-cyclopropyl-8-(3-hydroxyoxetan-3-yl)imidazo[1,2-a]pyridin-2-yl)methyl)-1H-pyrazole-4-carboxylate (890 mg, 56% yield) as a yellow solid. ESI-MS [M+H]+: 369.2. 1H NMR (400 MHz, DMSO-d6) delta8.41 (s, 1H), 8.30 (d, J=1.2 Hz, 1H), 7.90 (s, 1H), 7.70 (s, 1H), 6.45 (s, 1H), 5.50 (s, 2H), 5.24 (d, J=6.5 Hz, 2H), 4.66 (d, J=6.5 Hz, 2H), 3.74 (s, 3H), 1.94 (td, J=8.4, 4.2 Hz, 1H), 0.97-0.89 (m, 2H), 0.72-0.65 (m, 2H).

The synthetic route of 51105-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51105-90-9, name is Methyl 1H-pyrazole-4-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 51105-90-9, Application In Synthesis of Methyl 1H-pyrazole-4-carboxylate

To a stirred solution of methyl-1H-pyrazole-4-carboxylate (1.00 g, 6.134 mmol) in acetonitrile (20 mL) was added potassium carbonate (2.543 g, 18.40 mmol), and the mixture was stirred for 5 min at RT. To this mixture was added 2,4-dichloro-5-methylpyrimidine (0.773 g, 6.134 mmol), and the mixture was stirred at 80 C. overnight. The mixture was cooled and water (15 mL) was added, and the mixture was extracted with ethyl acetate (3*50 mL). The combined organic layer was dried over sodium sulfate, then evaporated under reduced pressure and the residue was purified by gradient column chromatography using ethyl acetate in n-hexane as eluent to give methyl 1-(2-chloro-5-methylpyrimidin-4-yl)-1H-pyrazole-4-carboxylate as a colorless solid (0.65 g, 42%). 1HNMR (400 MHz, CDCl3): delta 9.08 (s, 1H), 8.54 (s, 1H), 8.15 (s, 1H), 3.89 (s, 3H), 2.67 (s, 3H).

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Synthetic Route of 51105-90-9, 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 51105-90-9 as follows.

Potassium carbonate (822 mg, 5.95 mmol) was added to a solution of 2-(2-(benzyloxy)ethoxy)ethyl methanesulfonate (598 mg, 2.181 mmol) and methyl 1 H-pyrazole-4-carboxylate (250 mg, 1.982 mmol) in DMF (15 mE) and heated to 60 C. for 2 days. The reaction was cooled to it, diluted with EtOAc (50 mE) and washed sequentially with water (30 mE), sat. aq. NaHCO3 (30 mE) and 20% v/v brine (30 mE). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g column, 0-100% EtOAc/ isohexane) to afford the sub-title compound (472 mg) as a colourless oil.?H NMR (400 MHz, DMSO-d6) oe 8.33 (d, 1H),7.87 (d, 1H), 7.38-7.30 (m, 2H), 7.30-7.24 (m, 3H), 4.44 (s,2H), 4.32 (t, 2H), 3.80 (t, 2H), 3.72 (s, 3H), 3.58-3.53 (m,2H), 3.53-3.48 (m, 2H).mlz 305.1 (M+H) (ES)

According to the analysis of related databases, 51105-90-9, the application of this compound in the production field has become more and more popular.