Category: pyrazoles-derivatives

Synthetic Route of 1001020-14-9,Some common heterocyclic compound, 1001020-14-9, name is 3-(Trifluoromethyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C5H3F3N2O, 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.

e) 2-(2-(4-Formyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl)acetamido)-N-(2-hydroxyethyl)- 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide2-(2-Bromoacetamido)-N-(2-hydroxyethyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3- carboxamide (2.91 g, 8.06 mmol) was dissolved in DMF (25 ml.) and potassium carbonate (2.23 g, 16.11 mmol), followed by 3-(trifluoromethyl)-1 H-pyrazole-4-carbaldehyde (1.39 g, 8.46 mmol), added. The mixture was stirred at 60 0C for 25 min after which time the reaction mixture was diluted with water (-800 ml_), then acidified with 5 N HCI until pH 1. During acidification a free flowing solid was obtained which was collected by filtration. NMR analysis indicated ~60-70 % purity of desired product. The solid was succesfully triturated with a mixture of DCM/ether to give a light beige solid which was collected by filtration. The mother liquor was concentrated and a second batch obtained using a similar process. The batches were combined to yield the title product (1.76 g, 3.95 mmol, 49 %). MS (ESI) : m/z 443.5 [M – H]

The synthetic route of 1001020-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2008/3452; (2008); 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 138786-86-4 as follows. Application In Synthesis of Methyl 4-nitro-1H-pyrazole-3-carboxylate

Preparation of tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate (I); A solution of methyl 4-nitro-1H-pyrazole-3-carboxylate (54.0 g, 315.6 mmol), phenylboronic acid (77.0 g, 631.2 mmol), copper(II) acetate (86.0 g, 473.4 mmol) and pyridine (49.9 g, 631.2 mmol) in methylene chloride (600 mL) was stirred at ambient temperature open to air for 48 hours. The reaction was evaporated in vacuo, diluted with 1000 mL methylene chloride and filtered through a large plug of silica (washing with 2 liters methylene chloride). The solvent was evaporated in vacuo. 1H NMR (CDCl3) delta 8.61 (s, 1H), 7.73 (m, 2H), 7.50 (m, 3H), 4.02 (s, 3H).

According to the analysis of related databases, 138786-86-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berk, Scott C.; Close, Joshua; Hamblett, Christopher; Heidebrecht, Richard W.; Kattar, Solomon D.; Kliman, Laura T.; Mampreian, Dawn M.; Methot, Joey L.; Miller, Thomas; Sloman, David L.; Stanton, Matthew G.; Tempest, Paul; Zabierek, Anna A.; US2007/117824; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1260243-04-6, 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. 1260243-04-6 name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, 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 C.22 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid; a. A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160° C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0° C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52percent). White solid. MS (ISN) 316.3 [(M-H)-]; mp 190-192° C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 5-amino-1H-pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; McArthur, Silvia Gatti; Goetschi, Erwin; Wichmann, Juergen; Woltering, Thomas Johannes; US2007/72879; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 13808-64-5, These common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, 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.

10330] To a suspension of NaH 60% in oil (0.3 g; 7.45 mmol) in tetrahydrofuran (150 mE) there is added, at 100 C., 4-bromo-3-methyl-1H-pyrazole dissolved in 15 mE of tetrahydrofuran dropwise, over 15 minutes. Afier stirring for 40 minutes at ambient temperature, iodomethane (0.45 mE; 7.45 mmol) is added dropwise, and then the reaction mixture is stirred overnight. Afier adding water, the reaction mixture is evaporated and taken up in dichloromethane. The organic phase is separated off and dried over Mg504, filtered and concentrated to dryness. The residue is purified by chromatography over silica gel to yield a mixture of the title compounds (4-bromo-1 ,3-dimethyl-pyrazole and 4-bromo-1 ,5- dimethyl-pyrazole respectively in a ratio of 4:6).Step B: N-[4-[tert-Butyl(dimethyl)silyl]oxyphenyl]-1-methyl-pyrazol-4-amine To a solution of 30.8 g (0.137 mol) of the compound of Step A in 525 mL of anhydrous toluene there are successively added 29.8 g of sodium tert-butylate (0.310 mol), 4.55 g of Pd2(dba)3 (also referred to as tris(dibenzylideneacetone)dipalladium(0)) (4.96 mmol), 4.81 g of 2-di-tert-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (9.91 mmol) and 12.8 mL of 4-bromo-1-methyl-1H-pyrazole (0.124 mol). The batch is degassed under argon for 30 minutes and then refluxed for 3 hours. It is allowed to cool. The reaction mixture is concentrated to dryness and then taken up in dichloromethane, filtered over Celite and then concentrated to dryness again. The residue is then purified by chromatography over silica gel using dichloromethane and ethyl acetate as eluants to provide the expected product in the form of a solid.10333] The procedure is in accordance with Step B of Preparation 1?, replacing the 4-bromo-1 -methyl- 1H-pyra- zole by the mixture of isomers from Step A. A mixture of isomers in a ratio of 4:6 is obtained (respectively N-(4-{[tert- butyl(dimethyl)silyl]oxy}phenyl)-1 ,5-dimethyl- 1 H-pyrazol4-amine and N-(4-{ [tert-butyl(dimethyl)silyl]oxy}phenyl)1 ,3-dimethyl-1H-pyrazol-4-amine).

Statistics shows that 4-Bromo-3-methylpyrazole is playing an increasingly important role. we look forward to future research findings about 13808-64-5.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-1H-pyrazole, 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 2075-46-9, Formula: C3H3N3O2

At 0 C., to a solution of 4-nitropyrazole (3.3 g, 29.2 mmol) in anhydrous THF (30 mL) was added sodium hydride (1.3 g, 32.1 mmol). After the mixture was stirred for 1 hour, iodomethane (2 mL) was added slowly, and the resultant mixture was stirred for further 2 hours. Then the mixture was poured into ice water (100 mL), extracted with ethyl acetate (50 mL×3), and the organic layer was dried over anhydrous sodium sulfate. The mixture was filtrated, the filtrate was concentrated under reduced pressure. The residue was added into a component solvent (20 mL) of petroleum ether and ethyl acetate (20:1), stirred, and there was solid precipitated. After filtration, the solid was dried in vacuum for 8 hours to give white solid 15-b (2.6 g, yield: 70%), which was used directly for the next step without further purification. LC-MS (ESI): m/z=128 [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SHANGHAI CHEMEXPLORER CO., LTD.; XU, Zusheng; ZHANG, Nong; SUN, Qingrui; WANG, Tinghan; US2015/336982; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1260243-04-6, name is Ethyl 5-amino-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 1260243-04-6, category: pyrazoles-derivatives

Cs2CO3 (64.20 g, 197.20 mmol) was added to a solution of ethyl 5-amino-1H-pyrazole- 4-carboxylate (20.40 g, 131.40 mmol) and ethyl-3-ethoxyacrylate (28.6 mL, 197.20 mmol) in DMF (250 mL). The reaction mixture was stirred at 110 C for 16 h. The mixture was cooled to room temp and the pH was adjusted to 4 by the addition of AcOH (80 mL). The mixture was concentrated in vacuo and the residue partitioned between CH2Cl2 H2O (1000 mL, 1:1). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3 X 500 mL). The combined organics were washed with brine, dried (MgS04) and concentrated. The crude residue was suspended in EtOH (300 mL) and heated to boiling. After cooling to room temperature the solid was collected by filtration, rinsed with EtOH, then Et20 and dried under vacuum to give ethyl 5-oxo-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (25.16 g, 92 %). MS (ESI) calcd for C9H9N3O3 (m/z): 207.06; found: 208 [M+H]

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; CASAUBON, Rebecca, L.; NARAYAN, Radha; OALMANN, Christopher; VU, Chi, B.; WO2013/59587; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2033-45-6, name is 3,5-Dimethyl-4-iodopyrazole, 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 2033-45-6, Product Details of 2033-45-6

In a 50 ml reaction vessel under argon, a solution of crude 4-iodo-3,5-dimethyl-1 H- pyrazole x52 (1.15 g, 5.2 mmol) in 25 ml of dry CH2CI2 is added to 4- methylbenzenesulfonyl chloride (1.18 g, 6.2 mmol). Pyridine (0.42 ml, 5.2 mmol) is added EPO and the mixture is stirred for 16 h at room temperature. The organic phase is washed with water, dried over MgSOphi filtered and concentrated. The residue is purified by column chromatography on silicagel (Ch^C^/hexane: 70/30 (v/v)) to afford 4-iodo-3,5-dimethyl-1- [(4-methylphenyl)sulfonyl]-1H-pyrazole x53 (1.44 g).Yield : 74 %.LC-MS (MH+): 377.

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, 3,5-Dimethyl-4-iodopyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB S.A.; WO2006/128692; (2006); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 17635-45-9,Some common heterocyclic compound, 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, molecular formula is C9H9N3, 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: A mixture of aniline derivative 1a?1e (1 mmol) and 1 cm3concentrated hydrochloric acid was thoroughly stirred atroom temperature for 15 min and then cooled to 0 C. Asolution containing 0.069 g sodium nitrite (1 mmol) in 10 cm3 water was added dropwise to the initial mixtureduring 40 min. An aqueous solution of aromatic nucleophile(1 mmol) in NaOH 10percent (5 cm3) was then addedand the resulted mixture was stirred for 1 h at 0 C. Theprecipitated solid was filtered, washed with water and dried in air. The products 2a?2c, 2e, 2f, 2m, and 2o were purifiedby recrystallization in ethanol, but preparative TLC (nhexane?EtOAc, 4:1) was applied for purification of products2d, 2g?2l, 2n, and 2p.

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

Reference:
Article; Ghasemi, Zarrin; Azizi, Sajjad; Salehi, Roya; Kafil, Hossein Samadi; Monatshefte fur Chemie; vol. 149; 1; (2018); p. 149 – 157;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1260243-04-6, These common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-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.

Step 3: preparation of ethyl 5-acetamido-1 H-pyrazole-4-carboxylate. A mixture of ethyl 5-amino-1H-pyrazole-4-carboxylate (100 g, 0.65 mol) and acetyl chloride (441.2 g, 5.62 mol) at 0°C was heated to reflux for 4h. The reaction was concentrated in vacuo to remove excess acetyl chloride. Water (1.0 L) was added and the mixture was stirred for 16 h, after which it was filtered to afford the title compound as an off white solid (120g, 94percent). MS (M+H) m/z 198. 1H NMR (400 MHz, CDCI3) 6 ppm: 9.57(1 H, s), 7.75 (1H, s), 4.33-4.28 (2H, q, J = 7.08), 2.27 (3H, s), 1 .37-1.34 (3H, s).

The synthetic route of 1260243-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; SPRINGER, John Robert; DEVADAS, Balekudru; GARLAND, Danny James; GRAPPERHAUS, Margaret Lanahan; HAN, Seungil; HOCKERMAN, Susan Landis; HUGHES, Robert Owen; SAIAH, Eddine; SCHNUTE, Mark Edward; SELNESS, Shaun Raj; WALKER, Daniel Patrick; WAN, Zhao-Kui; XING, Li; ZAPF, Christoph Wolfgang; SCHMIDT, Michelle, Ann; WO2014/68527; (2014); 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 25222-43-9 as follows. COA of Formula: C4H6N2O

General procedure: To a solution of compound 6 (131 mg, 0.50 mmol) in DMF (2 mL) was added pyrazole (51 mg, 0.75 mmol), K2CO3 (138 mg, 1.00 mmol). The mixture was heated at 100 °C for 1 h. Reaction mixture was cooled, ice cold water (30 mL) was added and then extracted with EtOAc twice (30 mL × 2) and the combined organic layers were washed by saturated brine (30 mL). Then the organic layers were dried over Na2SO4, filtered and evaporated to afford the crude product used without further purification, To a solution of CF3COOH (1 mL) in CH2Cl2 (4 mL) was added the remaining solid (92 mg, 0.30 mmol). The mixture was at room temperature for 3 h, and then it was concentrated under reduced pressure to afford the crude product 19 used without further purification. To a solution of the product (99 mg, 0.30 mmol) in DMF (8 mL) was added 3-[(R)-1-(4-fluorophenyl)ethylaminocarbonyl]-5-[methyl (methylsulfonyl)amino]benzoic acid (106 mg, 0.27 mmol), EDCI (52 mg, 0.27 mmol), HOBt (37 mg, 0.27 mmol), DIPEA (99 muL, 0.60 mmol) was added and the mixture was allowed to react overnight at room temperature. Then the resulting mixture was diluted by 50 mL EtOAc and washed with dilute HCl aqueous solution (30 mL), saturated aqueous NaHCO3 (30 mL) and saturated brine (30 mL) sequentially. The organic layers were dried over Na2SO4 and evaporated to give the residue, which was purified by silica gel chromatography to afford 20 (149 mg, 91.3 percent).

According to the analysis of related databases, 25222-43-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Jia; Zou, Yiquan; Xu, Lei; Chen, Wuyan; Zhu, Yiping; Chen, Tiantian; Fu, Yan; Li, Li; Ma, Lanping; Xiong, Bing; Wang, Xin; Li, Jian; He, Jianhua; Zhang, Haiyan; Xu, Yechun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 270 – 283;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics