Category: 5744-59-2

Adding a certain compound to certain chemical reactions, such as: 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, 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 5744-59-2, Formula: C6H8N2O2

a) Ethyl 5-(l ,5-dimethyl-lH-pyrazol-3-yl)-l ,2,4-oxadiazole-3-carboxylateEthyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), 1,5 -dimethyl- 1H- pyrazole-3-carboxylic acid (95 %, 3.78 mmol, 0.530 g) and 1,3-diisopropylcarbodi- imide (4.16 mmol, 0.525 g) were suspended in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated and pyridine was added to the residue. The resulting mixture was refluxed for 6 h and stirred at RT overnight. Pyridine was evaporated and the residue diluted with DCM and water. The phases were separated and the water phase was extracted four times with DCM. The combined organics were washed with aqueous HC1 solution, saturated NaHC03, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.285 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-c¾): delta 1.43 (t, 3H), 2.30 (s, 3H), 4.23 (s, 3H), 4.49 (q, 2H), 6.96 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); 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 5744-59-2 as follows. Formula: C6H8N2O2

Example 85 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,5-dimethyl-1H-pyrazole-3-carboxamide In the same manner as in Example 259 and using 1,5-dimethyl-1H-pyrazole-3-carboxylic acid (145 mg, 1.0 mmol), tetrahydrofuran (5 mL), N,N-dimethylformamide (1 drop), oxalyl chloride (320 muL, 4.44 mmol), N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (250 mg, 0.77 mmol) and N,N-dimethylacetamide (7 mL) as starting materials, the title compound (57 mg, 17%) was obtained as a white solid. 1H-NMR (DMSO-d6, 300 MHz) delta 0.76-0.86 (4H, m), 1.87-1.97 (1H, m), 2.27 (3H, s), 2.30 (3H, s), 3.83 (3H, s), 6.53 (1H, s), 6.97-7.06 (2H, m), 7.25-7.34 (1H, m), 7.61 (1H, d, J=2.3 Hz), 7.92-7.97 (1H, m), 8.02 (1H, d, J=9.5 Hz), 9.35 (1H, s), 11.07 (1H, s).

According to the analysis of related databases, 5744-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); 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. 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid

Compounds 41-70 were part of a parallel set prepared in library plate format according to General Procedure L, outlined below. ; L. General Procedure for Plate Preparation-Amide Formation XXI: Resin bound deprotected biarylphenol XVII (prepared from intermediate XII, boronates XIVd and XIVe, following general procedures D-F) was distributed into a 96 well plate, 10 mg of resin (0.013 mmol) per well. To the resin 400 mul of dichloromethane was added, followed by 100 mul of DIEA, followed by 0.13 mmol (10 equiv) of heterocyclic carboxylic acid XXa-XXn was added followed by 61 mg (0.13 mmol, 10 equiv) of PyBrop. The plate was shaken at room temperature for 24 hours, then drained and washed with dichloromethane, methanol/dichloromethane, dimethylformamide, methanol/dichloromethane and dichloromethane. The compounds were cleaved with TFA/dichloromethane (600 mul, 1:1) into a 96 deep well plate and submitted for testing without further purification. (Mass spec results obtained are shown in Table 4). Carboxylic Acids Het-COOH XX:

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; Adolor Corporation; US2006/74086; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 5744-59-2, 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. 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step (b) N-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2- (3-iodophenoxy)nicotinamide To a suspension of N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(3-iodophenoxy Nicotinamide hydrochloride (1.5 g, 3.05 mmol) in acetonitrile (100 mL) was added 1,5-dimethyl-lH- pyrazole-3-carboxylic acid (1.069 g, 7.63 mmol) and triethylamine (4.25 mL, 30.50 mmol). 1- Propanephosphonic acid cyclic anhydride, 1.57M solution in THF (T3P) (5.83 mL, 9.15 mmol) was then added and the mixture stirred at RT for 2 h. The mixture was evaporated to dryness and the residue dissolved in DCM (150 mL) and washed with saturated NaHCO3 (aq), brine, dried (MgSO4) and evaporated to give a foam. The product was purified using column chromatography (eluent = neat EtOAc) to give the sub-title compound as a white foam. Yield: 1.04 g1H NMR (400 MHz, CDCl3) delta 8.36 (dd, J= 8.2, 3.1 Hz, IH), 8.07 (d, J= 3.1 Hz, IH), 7.87 (d, J= 6.7 Hz, IH), 7.64 (dt, J= 7.5, 1.5 Hz, IH), 7.55 (t, J= 1.8 Hz, IH), 7.22 – 7.14 (m, 2H), 6.69 (d, J= 7.7 Hz, IH), 6.53 (s, IH), 4.26 – 4.17 (m, IH), 4.12 – 4.03 (m, IH), 3.78 (s, 3H), 2.28 (s, 3H), 1.95 – 1.73 (m, 6H), 1.67 – 1.58 (m, 2H) MS: [M+H]+ = 578 (MultiMode+).

The synthetic route of 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/144494; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 5744-59-2, These common heterocyclic compound, 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, 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.

Step (c) N-((ls,4s)-4-(l,5-Dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4′-((4-isopropylpiperazin-l-yl)methyl)-2′-(morpholinomethyl)biphenyl-3- yloxy)nicotinamideA stirred solution of N-((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(4′-((4-isopropylpiperazin-l- yl)methyl)-2′-(morpholinomethyl)biphenyl-3-yloxy Nicotinamide hydrochloride (221 mg, 0.28 mmol), 1,5 -dimethyl- lH-pyrazole-3-carboxylic acid (39.2 mg, 0.28 mmol) and DIPEA (0.342 mL, 1.96 mmol) in DMF (10 mL) was treated with HATU (112 mg, 0.29 mmol) and stirred overnight. The solution was evaporated to remove most of the DMF and the residue was taken up in dichloromethane, was washed with water (3x), dried (TN^SC^) and evaporated. The residue was purified by reversed phase preparative HPLC on a Sunfire column, using a gradient of methanol in 0.1% aqueous TFA solution as eluent to give the title compound as a white solid. Yield: 110 mg1H NMR (400 MHz, DMSO) delta 10.18 – 9.97 (m, IH), 9.44 – 9.23 (m, IH), 8.36 (d, J= 6.4 Hz, IH), 8.27 (d, J= 3.1 Hz, IH), 8.04 – 8.00 (m, 2H), 7.65 – 7.61 (m, IH), 7.54 (t, J= 7.9 Hz, IH), 7.50 – 7.45 (m, IH), 7.36 (d, J= 7.9 Hz, IH), 7.29 (d, J= 8.2 Hz, IH), 7.22 – 7.14 (m, 2H), 6.59 (s, IH), 4.36 – 3.59 (m, 20H), 3.51 – 3.38 (m, 2H), 3.21 – 2.94 (m, 4H), 2.82 – 2.64 (m, IH), 2.52 – 2.38 (m, 2H), 2.14 (s, 3H), 1.84 – 1.60 (m, 8H), 1.25 (d, J= 6.4 Hz, 3H). MS: [M+H]+=767 (calc=767) (MultiMode+)

The synthetic route of 5744-59-2 has been constantly updated, and we look forward to future research findings.

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. 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H8N2O2

Example 2N-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2-(4′- hydroxy-2′-(morpholinomethyl)biphenyl-3-yloxy)nicotinamide Step (a) N-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3-carboxamido)cyclohexyl)-5-fluoro-2- (3-iodophenoxy)nicotinamideTo a solution of l,5-dimethyl-lH-pyrazole-3-carboxylic acid (0.123 g, 0.88 mmol) in dry DMF (10 mL) was added DIPEA (0.460 mL, 2.64 mmol) followed by HATU (0.334 g, 0.88 mmol). The mixture was allowed to stir for 10 min at RT. To this mixture was added N- ((ls,4s)-4-aminocyclohexyl)-5-fluoro-2-(3-iodophenoxy Nicotinamide (0.40Og, 0.88 mmol) and the mixture stirred overnight, poured onto water and the crude product collected by filtration, dried and used in step (c) without purification. [M+H]+ =577 (MultiMode+)

According to the analysis of related databases, 5744-59-2, the application of this compound in the production field has become more and more popular.

5744-59-2, 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. 5744-59-2, name is 1,5-Dimethyl-1H-pyrazole-3-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step (e) benzyl 4-(3-(3′-(3-((ls,4s)-4-(l,5-dimethyl-lH-pyrazole-3- carboxamido)cyclohexylcarbamoyl)-5-fluoropyridin-2-yloxy)biphenyl-3- yl)propyl)piperazine-l-carboxylate To a solution of benzyl 4-(3-(3′-(3-((ls,4s)-4-aminocyclohexylcarbamoyl)-5-fluoropyridin-2- yloxy)biphenyl-3-yl)propyl)piperazine-l-carboxylate (0.17 g, 0.26 mmol) and 1,5-dimethyl- lH-pyrazole-3-carboxylic acid (0.036 g, 0.26 mmol) in acetonitrile (2 mL) was added triethylamine (0.356 mL, 2.55 mmol). The initial suspension was left for 10 min to become a solution. 1.57M T3P in THF (0.171 mL, 0.27 mmol) was then added and the mixture stirred for 2 h. The solution was diluted with water and extracted with EtOAc. The organics were combined, dried (MgSO4) and concentrated in vacuo to give the sub-title compound as a white fluffy foam. Yield: 0.18g MS: [M+H]+=788 (MultiMode+)

The synthetic route of 5744-59-2 has been constantly updated, and we look forward to future research findings.