Month: July 2021

1203705-55-8, name is 3-Bromo-1H-pyrazol-5-amine, 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. HPLC of Formula: C3H4BrN3

A mixture of methyl 2-hydroxy-4-oxo-4-(pyridin-2-yl)but-2-enoate [1224740-13-9] (730 mg, 3.52 mmol) and 3-bromo-lH-pyrazol-5-amine [950739-21-6] (628 mg, 3.88 mmol) in MeOH (17 mL) was stirred under reflux for 18 h. The reaction mixture was cooled to rt and the precipitate was filtered off, rinsed with MeOH and dried. The residue (546 mg) was purified via achiral SFC (Stationary phase: Lux Cellulose-2 5 pm 250*30mm, mobile phase: 60% C02, 40% MeOH) to afford intermediate 1171 (147 mg, 13%) as a yellow solid.

The synthetic route of 1203705-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; LANCOIS, David Francis Alain; GUILLEMONT, Jerome Emile Georges; RABOISSON, Pierre Jean-Marie Bernard; ROYMANS, Dirk Andre Emmy; RIGAUX, Peter; MICHAUT, Antoine Benjamin; MERCEY, Guillaume Jean Maurice; (295 pag.)WO2019/106004; (2019); 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 82560-12-1 as follows. Recommanded Product: 82560-12-1

A suspension of Intermediate Rb (236 mg, 0.835 mmol), 3-tert-butyl-lH- pyrazole-5 -amine (Fluorochem, 122 mg, 0.88 mmol), copper(I) iodide (8.00 mg, 0.04 mmol), trans-N,N’-dimethylcyclohexane-l,2-diamine (23.8 mg, 0.17 mmol) and K2C03 (242 mg, 1.75 mmol) in degassed toluene (1 mL) was stirred at 100C under Ar for 3 h, and then heated to 150 C for 5 h using microwave irradiation. The cooled solution was partitioned between EtOAc (10 mL), water (5 mL) and concentrated aqueous ammonia (5 mL). The aqueous layer was extracted with EtOAc (10 mL), then the combined organics washed with water (10 mL), brine (10 mL), dried (Na2S04), filtered and concentrated in vacuo to leave a oil (305 mg). FCC, using 20-45%) EtOAc in cyclohexane, gave the title compound as an opaque sticky gum (129 mg, 53%). LCMS (Method 3): Rt 2.80 min, m/z 294 [MH+].

According to the analysis of related databases, 82560-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3112-31-0, name is 1H-Pyrazole-3,5-dicarboxylic 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 3112-31-0, name: 1H-Pyrazole-3,5-dicarboxylic acid

The mixture solution of Cu(NO3)2*3H2O (0.2 mmol, 48 mg), 4,4′-bipyridine (0.2 mmol, 31 mg) and pyrazole-3,5-dicarboxylic acid(0.2 mmol, 35 mg) in the deionized water (7 mL), DMF (2 mL)and ethanol (3 mL) was sealed in a 20 mL glass vial. Then, the mixturewas heated at 120° C for 1 day and then slowly cooled down toroom temperature. The blue crystals of 3 were obtained. Yield:10 mg (16percent) based on copper salt Anal. Calcd for Cu5C50H46N14O24:C, 38.88; H, 3.00; N, 12.69. Found: C, 38.79; H, 2.85; N, 13.00percent. FTIRpeaks (KBr, cm-1): 3368br (m(OH)), 1646s (mas(OCO)), 1599s (m(CN)), 1533w, 1481w, 1407w, 1387m (ms(OCO)), 1288s, 1224m,1065w, 1020w, 817w, 806w, 778 m. UV-vis (diffuse reflectance,cm-1): 14407.

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:
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

Reference of 27006-76-4, The chemical industry reduces the impact on the environment during synthesis 27006-76-4, name is 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, I believe this compound will play a more active role in future production and life.

General procedure: To a well stirred solution of substituted phenol (30 mmol) in DMF or DMSO (30 mL), KOH wasadded (40 mmol) at room temperature. The resulting mixture was heated to 40 C for 2-4 h, and thencompound 1 (20 mmol) was added thereto. The reaction solution was heated to 105 C for 8-24 h.After being cooled to room temperature, the mixture was poured into water and extracted with ethylacetate (3 50 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered,and evaporated to afford intermediate 2, with yields ranging from 52% to 76% [25].

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, 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Hong; Yao, Wei; Fang, Yuan; Sun, Siyu; Shi, Yujun; Chen, Jia; Jiang, Guoqing; Shi, Jian; Molecules; vol. 22; 12; (2017);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

52222-73-8, name is 4-(Trifluoromethyl)-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. Quality Control of 4-(Trifluoromethyl)-1H-pyrazole

[1615] a mixture of 4-(trifluoromethyl)-1H-pyrazole compound (1 g, 7.35 mmol), 2-chloropyrimidine (926 mg, 8.09 mmol) and K2CO3 (2.03 g, 14.7 mmol) in DMF(15 ml) was heated to 110 C for 12 hr. The mixture was added water (20 ml) and extracted with ethyl acetate (20 ml x 2), the organic phases were washed with brine (10 ml), dried over Na2SO4, filtered and concentrated. The residue was recrystallized by mtbe to give compound 410a (800 mg, yield: 50.8%) as yellow solid. 1H NMR (400mhz, CDCl3) delta 8.94 (s, 1h), 8.83 (d, 7 = 4.8 hz, 2h), 8.03 (s, 1h), 7.34 (t, 7 = 4.8 hz, 1h).

The synthetic route of 52222-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); 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. 7119-95-1, name is 1-Nitropyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C3H3N3O2

A 100mL one-neck flask equipped with a magnetic stirrer was added 5g of compound 1 and 15mL acetic acid, stirred, to give a clear solution. Under ice bath 3.5mL of fuming nitric acid was slowly added dropwise to the mixed solution, maintaining vigorous stirring, the reaction temperature does not exceed 30 deg. C. 10mL acetic anhydride was added to the mixture, after the addition, the mixture immediately became cloudy, to give a white turbid liquid. After the addition it was stirred at room temperature, until the solution became clear, about 2.5h. After completion of the reaction, the solution was slowly poured into 100mL crushed ice and with vigorous stirring, potassium carbonate was added portionwise until the mixture was neutral, white precipitate was filtered to give 5.6g of white powdery crystals, the filtrate was extracted with ethyl acetate, the combined organic phase was dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporation to give pale yellow crystals 1.3490g, total crude was 6.9490g, yield 91.9percent recrystallized from benzene. Weigh three 100mg compound 2 into thick-walled pressure bottle, gradually heated to 160 deg. C, 180 deg. C, 200 deg. C, the reaction at this temperature for 1 ~ 3h to obtain compound 3, the results shown in Table 1.

The synthetic route of 7119-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Institute of Technology; Zhou, Zhiming; Tao, Wenchang; Zhang, Jun; (6 pag.)CN105669557; (2016); A;,
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

Related Products of 5932-27-4, 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. 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 16: Ethyl 1 -U2-(putyloxy)phenyl1methyl’HH-pyrazole-3- carboxylate; To ethyl 1 H-pyrazole-3-carboxylate (1.74 g, 12.4 mmol, ChemCollect GmbH) and potassium carbonate (3.43 g, 24.8 mmol) was added 1-(bromomethyl)-2- (butyloxy)benzene (3.0 g, 12.3 mmol) as a solution in DMF, washing in with further DMF to give a total volume of 35 ml. The mixture was stirred under nitrogen at ambient temperature. After 24 h the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and water (approximately 100 ml each). The layers were separated and the aqueous was extracted with further EtOAc (2 x 50 ml). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give a pale yellow oil, which partially solidified on standing. The material was loaded in dichloromethane and purified on silica (Si) 100 g using 0- 100percent ethyl acetate-cyclohexane. The appropriate fractions were combined and concentrated in vacuo to give the title compound (2.07 g); LCMS: (System 4) MH+ = 303, tRET = 3.27 min.

The chemical industry reduces the impact on the environment during synthesis Ethyl 1H-pyrazole-3-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (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. 59340-27-1, name is 1,3,5-Trimethyl-1H-pyrazole-4-sulfonyl chloride belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

E. General coupling protocol for the synthesis of compounds with general structure (249)Exemplified by the synthesis of N-((ls,4s)-4-fluoro-4-(3-(trifluoromethyl)phi sulfonyl)cyclohexyl)- 1 , 3, 5-trimethyl- lH-pyrazole-4- sulfonamide (251) [00330] Cis-4-fluoro-4-(3-(trifluoromethyl)phenylsulfonyl)cyclohexanamine (110) (75 mg, 0.21 mmol), TEA (111 mu,, 0.8 mmol), and l,3,5-trimethyl-lH-pyrazole-4- sulfonyl chloride (250) (0.21 mmol) were stirred at room temperature for 16 hours. The reaction was concentrated in vacuo and the crude material purified by reverse phase HPLC to give N-(Cis-4-fluoro-4-(3-(trifluoromethyl)phenylsulfonyl)cyclohexyl- 1 ,3,5-trimethyl- lH-pyrazole-4- sulfonamide (251).

The synthetic route of 59340-27-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZALICUS PHARMACEUTICALS LTD.; PAJOUHESH, Hassan; GALEMMO, Robert; HOLLAND, Richard; ZHOU, Yuanxi; ZHU, Yongbao; SIMONSON, Eric; CHAHAL, Navjot; GRIMWOOD, Mike; WO2011/35159; (2011); 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. 1018446-95-1, name is tert-Butyl 4-amino-1H-pyrazole-1-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of tert-Butyl 4-amino-1H-pyrazole-1-carboxylate

To a stirred mixture of tert-butyl 4-amino-1H-pyrazole-1 -carboxylate (512 mg, 2.795 mmol) and bis(2-bromoethyl) ether (778 mg, 3.354 mmol) in DMF (28 mL) was added DIPEA (1 .46 mL, 8.384 mmol) and the resulting solution was stirred at 90C for 16h.The reaction mixture was diluted with AcOEt, washed twice with water and then with brine, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified on silica gel (DCM/acetone: 100/0 to 80/20) to provide intermediate (20a) (282 mg, 1 .1 13 mmol, 40%) as a light-brown solid. MS m/z ([M+H]+) 254. 1 H NMR (400 MHz, DMSO-d6): (ppm) 1 .55 (s, 9H), 2.93 (dd, J = 5.1 , 4.2 Hz, 4H), 3.69 (dd, J= 5.1 , 4.2 Hz, 4H), 7.62 (d, J= 0.7 Hz, 1 H), 7.74 (d, J= 0.7 Hz, 1 H) .

The synthetic route of 1018446-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MUTABILIS; BARBION, Julien; CARAVANO, Audrey; CHASSET, Sophie; CHEVREUIL, Francis; FAIVRE, Fabien; LEBEL, Remi; LECOINTE, Nicolas; LEDOUSSAL, Benoit; LE-STRAT, Frederic; SIMON, Christophe; OLIVEIRA, Chrystelle; LE FRALLIEC, Geraldine; BRIAS, Julie; FARESCOUR, Laurence; VOMSCHEID, Sophie; RICHARD, Sebastien; (219 pag.)WO2018/60481; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics