Tag: M.W:100-200

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 176969-34-9

Add a 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (30.0 mmol) and 10 mL of sulfoxide to a 100 mL reaction flask, and heat to reflux. After waiting for the reaction solution to change from turbid to clear, continue to react for 30 minutes.Stop heating and concentrate to remove excess sulfoxide,1-methyl-3-difluoromethyl-1H-pyrazole-4-formyl chloride represented by the formula (V-1) was obtained, and it became a solid after cooling.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Guo Changfei; Jin Tao; Tan Chengxia; Weng Jianquan; Wu Hongke; (20 pag.)CN110615765; (2019); A;,
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. 121507-34-4, name is 5-Isopropoxy-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H11N3O

To a mixture of 2,3,6-trichloro-5-nitropyridine (2.61 g, 11.4 mmol) and DIEA (1.90 ml, 11.4 mmol) in THF (50 ml) was added 5-isopropoxy-l/J-pyrazol-3-amine (1.20 g, 8.50 mmol) at 0 0C. After addition, the reaction mixture was stirred at 25 C for 5 days. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane-EtOAc = 1 : 1) to give the title compound as a yellow solid (0.51 g, 18%). 1H NMR (400 MHz) delta 12.22 & 11.35 (s, IH), 10.12 & 9.80 (s, IH), 8.64 & 8.54 (s, IH), 5.95 & 5.84 (s, IH), 4.70 & 4.46 (m, IH), 1.27-1.32 (m, 6H). MS: Calcd.: 331; Found: [M+H]+ 332.

The synthetic route of 121507-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/87538; (2006); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

2458-26-6, name is 3-Phenyl-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. Application In Synthesis of 3-Phenyl-1H-pyrazole

6.15. Synthesis of (S)-2-Amino-3-[4-(2-amino-6-{2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethoxy}-pyrimidin-4-yl)-phenyl]-propionic acid 2,2,2-Trifluoro-1-(2-iodo-phenyl)-ethanol (0.331 g, 1.1 mmol), 3-phenyl pyrazole (0.144 g, 1.0 mmol), CuI (0.019 g, 0.1 mmol), K2CO3 (0.290 g, 2.1 mmol), (1R,2R)-N,N’-dimethyl-cyclohexane-1,2-diamine (0.028 g, 0.2 mmol) and toluene (10 ml) were taken in a 20 ml pressure tube and the mixture was heated at 130 C. (oil bath temperature) for 12 h. The mixture was diluted with ethyl acetate and washed with H2O (2*20 ml), brine, and dried over sodium sulfate. Removal of solvent gave a crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to afford 2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol (75 mg).

The synthetic route of 2458-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jin, Haihong; Shi, Zhi-Cai; Tunoori, Ashok; Wang, Ying; Zhang, Chengmin; Devasagayaraj, Arokiasamy; US2008/153852; (2008); 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. 660845-30-7, name is 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde

In an autoclave, 10 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde were dissolved in 150 ml of ethanol, and 10.4 g of triethylamine and 500 mg of 5% palladium on calcium carbonate were added. The autoclave was flushed with nitrogen and subsequently pressurised to 5 bar hydrogen. The reaction mixture was then stirred at 30 C. for 4 h. After filtration of the catalyst, the solvent was removed under reduced pressure and the product was obtained as a solid (7.4 g) having a melting point of 46-47 C. 1H NMR (CDCl3) 4.1 (s, 3H), 6.85 (t, 1H), 7.73 (s, 1H), 10.1 (s, 1H) ppm.

The synthetic route of 660845-30-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pazenok, Sergii; Lui, Norbert; Mueller, Thomas Norbert; US2015/126748; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 578008-32-9, A common heterocyclic compound, 578008-32-9, name is tert-Butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate, molecular formula is C9H15N3O2, 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 D: To 4-chloro-2-[difluoro-(5-fluoro-pyridin-2-yl)-methyl]-8-bromo-quinazoline (0.19 g, 0.49 mmol) in DMA (1.0 mL) were added 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.30 g, 1.53 mmol) and HOAc (0.065 mL, 1.1 mmol) and the mixture was heated to 100 C. for 5 h. The mixture was allowed to cool to rt and purified by reverse phase HPLC (ammonium acetate modifier). Fraction 1 containing pure product was treated with saturated aq NaHCO3 (2-4 mL) and concentrated under reduced pressure. The aqueous residue was extracted with DCM (3×30 mL) and the combined extracts were washed with sat aqueous NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated to dryness under reduced pressure to afford 8-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine (48 mg, 20%) as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 12.22 (br s, 1H), 10.87 (br s, 1H), 8.57-8.81 (m, 2H), 8.24 (d, J=7.5 Hz, 1H), 8.02 (d, J=5.3 Hz, 2H), 7.54 (t, J=7.9 Hz, 1H), 5.95 (s, 1H), 2.17 (s, 3H); LC-MS (ESI) m/z 449/451 (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.

Reference:
Patent; Hadd, Michael J.; Holladay, Mark W.; Rowbottom, Martin; US2012/53174; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 3112-31-0,Some common heterocyclic compound, 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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: The deionized water (3 mL) was slowly dropped over the mixturesolution containing Cu(NO3)23H2O (0.2 mmol, 48 mg) andpyrazine (0.2 mmol, 16 mg) in water and DMF (4 mL, 1:1 v/v) in15 mL of glass vial. Then, the solution of pyrazole-3,5-dicarboxylicacid (0.2 mmol, 35 mg) in deionized water and ethanol (5 mL,1:1 v/v) was carefully layered over the mixture layer. Then, the vialwas sealed and allowed to stand undisturbed at room temperature. The blue crystals of 1 were obtained after 2 days.

The synthetic route of 3112-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Klongdee, Fatima; Boonmak, Jaursup; Moubaraki, Boujemaa; Murray, Keith S.; Youngme, Sujittra; Polyhedron; vol. 126; (2017); p. 8 – 16;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 25016-11-9, name is 1-Methyl-1H-pyrazole-4-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. name: 1-Methyl-1H-pyrazole-4-carbaldehyde

Step 2) Potassium t-butoxide (23.47 g, 199.1 mmol, 2.44 eq.) was suspended in anhydrous DME (90 mL) and cooled to – 60C. Tosyl methyl isocyanide (23.76 g, 121.7 mmol, 1.49 eq.) was dissolved in anhydrous DME (75 mL) and the solution was added drop- wise to the potassium t-butoxide solution over 20 minutes. After stirring for 20 minutes between – 60 and – 55C, the aldehyde from Step 1 in anhydrous DME (55 mL) was added over 23 minutes. The reaction was stirred for one hour at – 55 to – 50C, and then methanol (90 mL) was added. The cooling bath was removed, and after stirring for 5 minutes in air, the reaction flask was immersed in an oil bath preheated to 85C. The reaction was stirred for 1 hour. After cooling, the mixture was concentrated and the resulting tan solid was dissolved in water (180 mL) with acetic acid (9 mL). This was extracted with ethyl acetate (3 x 250 mL), and these extracts were combined, washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to yield a brown oil (13.71 g). This oil was dissolved in dichloromethane and purified by silica-gel chromatography using a gradient from 0% to 15% dichloromethane-acetone to yield a bright yellow oil in 63% yield (7.89 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25016-11-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHUMWAY, Stuart Denham; TONIATTI, Carlo; ROBERTS, Brian Scott; MARTIN, Melissa M.; WO2013/39854; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 89202-89-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 89202-89-1 name is 1,4-Dimethyl-1H-pyrazole-3-carboxylic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 209 Production of N-[5-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)-2-methylphenyl]-1,4-dimethyl-1H-pyrazole-3-carboxamide Using N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (323 mg, 1.0 mmol), 1,4-dimethyl-1H-pyrazole-3-carboxylic acid (154 mg, 1.1 mmol) tetrahydrofuran (2.0 mL), N,N-dimethylformamide (1 drop), thionyl chloride (0.08 mL, 1.1 mmol) and N,N-dimethylacetamide (6.0 mL), and by a reaction in the same manner as in Example 203, the title compound (208 mg, 47%) was obtained as pale-yellow crystals. 1H-NMR (DMSO-d6, 300 MHz) delta 0.75-0.85 (4H, m), 1.85-2.00 (1H, m), 2.20 (3H, s), 2.28 (3H, s), 3.88 (3H, s), 6.95-7.05 (1H, m), 7.02 (1H, d, J=9.6 Hz), 7.30 (1H, d, J=8.7 Hz), 7.63 (1H, s), 7.65-7.70 (1H, m), 7.93 (1H, s), 8.02 (1H, d, J=9.6 Hz), 9.28 (1H, s), 11.06 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dimethyl-1H-pyrazole-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/137595; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-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. Recommanded Product: 1-Methyl-1H-pyrazole-5-carboxylic acid

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (compound 4A, 4.58 g, 36.3 mmol), DIEA (13.7 g, 106 mmol) in CH2Cl2 (30 mL) was added EDCI (11.6 g, 60.5 mmol) and DMAP (4.44 g, 36.3 mmol) at -5 C., the mixture was stirred at -5 C. for 30 min. Then methyl 4-amino-3-methylbenzoate (compound 11, 5.00 g, 30.3 mmol) was added, stirred at -5 C. for 30 min. The mixture was warmed to 25 C., stirred for 11 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.52) showed starting material consumed completely. The mixture was concentrated in vacuum to give light yellow oil. The oil was purified by silica gel column chromatography (petroleum ether:ethyl acetate=90:10 to 50:50) to give methyl 3-methyl-4-(1-methyl-1H-pyrazole-5-carboxamido)benzoate (compound 12, 5.70 g, 69% yield) as light yellow solid.

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

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 129768-28-1, 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 129768-28-1 as follows.

General procedure: To a mixture of D-a (100 mg, 0.46 mmol), acid (0.56 mmol), HATU (262 mg, 0.69 mmol) and N, /V-diisopropylethylamine (118 mg, 0.92 mmol) i n N, A’-d i m e th y 1 fo rm am i dc (3 mL) was stirred at 25 C for 2-24 h. The mixture was diluted by the addition of water, followed by General Work-up Procedure 1. The residue was purified by prep-HPLC or flash column chromatography to afford the desired product. The amide bond formation reaction was carried out in a similar fashion as for 184 using 3-(trifluoromcthyl)- l//-pyrazolc-5-carboxylic acid (61 mg, 0.34 mmol, 1.5 eq.) and D-a (50 mg, 0.23 mmol, 1 eq.) as reactants afforded the title compound (trifluoroacetic acid salt, 63 mg, 56%) as an off-white solid: 1H NMR (500 MHz, DMSO-ri6) 14.58 (d, J = 32.8 Hz, 1H), 10.26 (s, 1H), 8.78 (s, 1H), 7.54 (s, 2H), 7.47 (s, 1H), 7.25 (t, J = 7.8 Hz, 1H), 7.03 – 6.97 (m, 1H), 3.52 (s, 3H), 3.22 (h, J = 6.8 Hz, 1H), 3.12 – 3.02 (m, 2H), 1.25 (d, J = 6.9 Hz, 3H); LCMS: C17H17F3N6O requires: 378, found: m/z = 379 [M+H]+.

According to the analysis of related databases, 129768-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics