Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 23170-45-8, name is Methyl 3-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 23170-45-8, Recommanded Product: Methyl 3-methyl-1H-pyrazole-4-carboxylate

Methyl 3-methyl-1-(1-phenylethyl)-1H-pyrazole-4-carboxylate. To a solution of methyl 3-methyl-1H-pyrazole-4-carboxylate (280 mg, 2 mmol) in DMF (30 mL) was added (1-bromoethyl)benzene (0.37 g, 2 mmol) and potassium carbonate (0.55 g, 4 mmol). The mixture was stirred at 20 C and stirred for 12 h. The solvent was evaporated in vacuo and the residue was purified by HPLC (Column: Dsisol, 10mu, C18, 250 mm x 50 mm; Mobile: acetonitrile (0.1% formic acid)-water (0.1% formic acid), acetonitrile from 30 to 70 in 80 minutes; oven: 20 C; flow rate: 50 mL/minute, wavelength: 214 nm) to give methyl 3-methyl-1-(1-phenylethyl)-1H-pyrazole-4-carboxylate (90 mg, 19%, desired) and methyl 5-methyl-1-(1-phenylethyl)-1H-pyrazole-4-carboxylate (80 mg, 16%). The product was used for the next step directly.

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, Methyl 3-methyl-1H-pyrazole-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gehling, Victor S.; Vaswani, Rishi G.; Nasveschuk, Christopher G.; Duplessis, Martin; Iyer, Priyadarshini; Balasubramanian, Srividya; Zhao, Feng; Good, Andrew C.; Campbell, Robert; Lee, Christina; Dakin, Les A.; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Audia, James E.; Cummings, Richard T.; Normant, Emmanuel; Trojer, Patrick; Albrecht, Brian K.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3644 – 3649;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 124004-31-5, The chemical industry reduces the impact on the environment during synthesis 124004-31-5, name is 5-Amino-1H-pyrazole-3-carboxylic acid, I believe this compound will play a more active role in future production and life.

General procedure: The corresponding amino acid2, 4 (0.0173 mol) was dissolved in 2 aqueous l (50 ml),and the formed solution was cooled to 0 in an ice bath.Aqueous NaNO2 (0.019 mol) was dropwise added to thereaction mixture. The mixture was stirred for 30 min, thenaqueous NaN3 (0.026 mol) was carefully added. Thereaction mixture was stirred for 3-4 h. The formed precipitatewas filtered off on a fritted glass filter and washed witha small amount of H2O, then dried in a vacuum desiccatorover P2O5 to constant weight. The filtrate was extractedwith EtOAc, the organic phase was separated and driedover anhydrous Na2SO4. The dried organic phase wasevaporated under reduced pressure on the rotary evaporatorto afford a solid. Both solids were combined.5-Azido-1-pyrazole-3-carboxylic acid (5). Yield 2.32 g(87%), yellow solid, mp 164-165. IR spectrum, nu, cm-1:3309 (NH), 3101 (OH), 2125 (N3), 1675 (C=O). 1H NMRspectrum (400 MHz, DMSO-d6), delta, ppm: 13.76 (2, br. s,NH, COOH); 6.48 (1H, s, -4 pyrazole). 13C NMRspectrum (101 MHz, DMSO-d6), delta, ppm: 160.3; 147.6;136.9; 98.9. Found, m/z: 154.0363 [M+H]+. C4H4N5O2.Calculated, m/z: 154.0360. Found, %: C 31.51; H 1.82;N 45.37. 4H3N5O2. Calculated, %: C 31.38; H 1.98;N 45.74.

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-Amino-1H-pyrazole-3-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dalinger, Aleksander I.; Medved?ko, Alexey V.; Balalaeva, Alexandra I.; Vatsadze, Irina ?.; Dalinger, Igor L.; Vatsadze, Sergey Z.; Chemistry of Heterocyclic Compounds; vol. 56; 2; (2020); p. 180 – 191;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 930-36-9, 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. 930-36-9, name is 1-Methylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The (1 -methyl-1 H-pyrazol-5-yl)acetic acid used in the above procedure was prepared as follows: (i) 1 -Methyl-1 H-pyrazole-5-carbaldehyde was prepared as follows (c.f. Bioorg. Med. Chem., 2001 , 9, 961-982): A solution of 1 -methyl- 1 H-pyrazole (11.0 g, 0.134 mol) in tetrahydrofuran (200 ml) was stirred at -700C under argon. n-Butyl lithium (2.5 M in hexanes, 58.8 ml, 0.147 mol) was added dropwise maintaining the internal reaction temperature below -600C. The mixture was cooled to -700C and N, N- dimethylformamide (40 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight. The mixture was cooled to 00C and water (200 ml) was added followed by ethyl acetate (300 ml). The organic layer was separated and the aqueous layer was re-extracted with ethyl acetate. The combined organic extracts were washed with water, brine, then dried and evaporated. The residue was purified by flash chromatography on silica gel eluting with 0-100% ethyl acetate in hexanes to afford 1 -methyl-1 H-pyrazole-5-carbaldehyde which was used in the next step.

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, 1-Methylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/125600; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1031351-95-7, 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. 1031351-95-7 name is Methyl 3-formyl-1-methyl-1H-pyrazole-5-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.

Step 2: To a solution of the chloro-phosphonium salt (2.9 g, 5.95 mmol) in dry THF (20 mL) at – 78 0C was added LiHMDS (6.54 mL, 6.54 mmol) and the resulting mixture stirred at -78 0C for 1 h. The mixture was then warmed up to room temperature and a solution of lH-pyrazole-5- carboxylic acid, 3-formyl-l -methyl-methyl ester (1.0 g, 5.95 mmol) in dry THF (15 mL) was added and the resulting mixture stirred for 2 h. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (2 x 40 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate 1 :0 to 9:1) afforded, two products, 5-{(Z)-2-[3-(4- fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl} -2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (400 mg) and ethyl 5-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-vinyl}-2- methyl-2H-pyrazole-3-carboxylic acid methyl ester (2.15 g) as off white solids.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127975; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 119083-00-0, A common heterocyclic compound, 119083-00-0, name is 1-Methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid, molecular formula is C6H5F3N2O2, 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.

Example 159 N-(4-{trans-2-[(cyclopropylmethyl)amino]cyclopropyl}phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide hydrochloride By a method similar to Example 80, the title compound (56.1 mg) was obtained from tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (82.8 mg) and 1-methyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (63.8 mg). MS (API+): [M+H]+ 379.3. 1H NMR (300 MHz, DMSO-d6) delta 0.29-0.40 (2H, m), 0.52-0.62 (2H, m), 0.95-1.11 (1H, m), 1.18-1.30 (1H, m), 1.39-1.52 (1H, m), 2.32-2.47 (1H, m), 2.82-3.02 (3H, m), 3.98 (3H, s), 7.14 (2H, d, J = 8.6 Hz), 7.61 (2H, d, J = 8.6 Hz), 8.54 (1H, s), 9.01 (2H, brs), 10.12 (1H, s).

The synthetic route of 119083-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; TOMITA, Naoki; KAJII, Shigeo; CARY, Douglas Robert; TOMITA, Daisuke; IMAMURA, Shinichi; TSUCHIDA, Ken; MATSUDA, Satoru; HARA, Ryujiro; EP2743256; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 16082-33-0, A common heterocyclic compound, 16082-33-0, name is 1H-Pyrazole-3,5-diamine, molecular formula is C3H6N4, 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.

To a solution of 1H-pyrazole-3,5-diamine (70 mg, 0.54 mmol) prepared by the procedure described in the literature (US82902, 2007) and pyridine (2.0 mL) was added III (100 mg, 0.20 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure. The residue was purified by column chromatography (silica, 0-40% CMA in CH2Cl2) followed by preparative HPLC to afford the title compound (25 mg, 25%) as an off-white solid. [0527] Rf0.20 (180:18:2 Methylene Chloride/Methanol/concentrated Ammonium Hydroxide). 1H NMR (300 MHz, DMSO-d6) delta 0.83 (s, 3H), 0.92 (s, 3H), 0.95 (s, 3H), 1.0 (s, 3H), 1.25 (s, 6H), 1.30 (s, 3H), 1.30-1.90 (m, 23H), 2.06 (m, 3H), 2.25 (m, 1H), 2.44 (d, J = 15.0 Hz, 1H), 2.62 (m, 1H), 5.35 (s, 1H). mp >300C. APCI MS (Positive Mode) m/z 574 [C34H51N7O + H]+

The synthetic route of 16082-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sequoia Sciences, Inc.; Eldridge, Gary R.; Buckle, Ronald Neil; Ellis, Michael; Huang, Zhongping; Reilly, John Edward; EP2712863; (2014); 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. 25699-83-6, name is 4-(1H-Pyrazol-1-yl)benzonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-(1H-Pyrazol-1-yl)benzonitrile

A 250-mL round-bottom flask was charged with 4-(1H-pyrazol-1-yl)benzonitrile (Step 1, 2 g, 11.82 mmol), ethanol (40 mL), water (40 mL) and sodium hydroxide (705 mg, 17.63 mmol,). The resulting solution was stirred at 105 C. 16 h and then concentrated under vacuum. The residue was diluted with water (30 mL) and extracted with ethyl acetate (50 mL). The pH of the aqueous phase was adjusted to 5 with hydrochloric acid (6.0 M). The solids were collected by filtration, washed with water (10 mL) and dried in an oven to afford 4-(1H-pyrazol-1-yl)benzoic acid as a light yellow solid (Intermediate 2-13, 1 g, 45%). LCMS: (ESI) m/z 189 [M+H].

The synthetic route of 25699-83-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; (61 pag.)US2016/185786; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)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. name: Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

(S)-Benzyl 5-(hydroxymethyl)-2,3-dihydro-7/-/-inden-2-ylcarbamate (2.96 mmol, 880mg) was dissolved in DCM (10 ml.) and thionyl chloride (5.92 mmol, 0.432 ml, 704 mg) added. The mixture was stirred at room temperature for 30 min TLC before the solvent was removed under reduced pressure and residual thionylchloride azeotroped with DCM (x3). To the residue was added potassium carbonate (8.88 mmol, 1227 mg) followed by DMF (8 ml) then ethyl 3-(trifluoromethyl)-7/-/-pyrazole-4-carboxylate (2.96 mmol, 616 mg) and the mixture heated to 60 0C. After 1 h the mixture was concentrated and partitioned between EtOAc/H2O and the organic layer was washed with water (x 3). The organic layer was dried, filtered and concentrated to give a yellow oil which was purified by flash chromatography eluting with 15% EtOAc/Heptane to give the desired isomer as a colourless oil (45 mg, 0.092 mmol, 3.1%). 1H NMR (400 MHz, CDCI3) delta 1.34 (t, 3H) 2.75 (m, 2H) 3.25 (m, 2H) 4.33 (q, 2H), 4.50 (m, 1 H) 4.95 (m, 1 H), 5.08 (s, 2H) 5.48 (s, 2H) 7.00 (m, 2H) 7.15 (d, 1 H) 7.34 (m, 5H) 7.99 (s, 1 H).

The synthetic route of Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 14521-80-3, name is 3-Bromo-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H3BrN2

Reference Production Example 4; (1) A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 ml of N,N-dimethylformamide was stirred at 100C for 8 hours. After the reaction mixture was cooled to room temperature, water was poured into the reaction mixture. The reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridine 1H-NMR (CDCl3, TMS) delta (ppm): 6.51 (1H, d, J=2Hz), 7.31 (1H, dd, J=8Hz, 4Hz), 7.91 (1H, dd, J=8Hz, 1Hz), 8.04 (1H, d, J=2Hz), 8.45 (1H, dd, J=4Hz, 1Hz)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14521-80-3.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2143720; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 852227-86-2, These common heterocyclic compound, 852227-86-2, name is 5-(Chloromethyl)-1,3-dimethyl-1H-pyrazole, 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.

D-15 D-16Step 4. A mixture of D-15 (210 mg, 0.78 mmol) and cesium carbonate (765 mg, 2.35 mmol) in DMF (25 mL) was heated to 60C with stirring then a solution of 5-(chloromethyl)-1 ,3-dimethyl-1 H-pyrazole (1 13 mg, 0.78 mmol) in DMF(10 mL) was added drop wise. The reaction mixture was stirred for 1 hour at 60C. The solids were removed by filtration and the solvent was removed under reduced pressure. Crude D-16 was used as such in the next step.LC-MS: Anal. Calcd. For CisHasNeOs: 376.22; found 377 [M+H]+

The synthetic route of 852227-86-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner; JONCKERS, Tim, Hugo, Maria; LAST, Stefaan, Julien; PIETERS, Serge, Maria, Aloysius; VLACH, Jaromir; WO2012/136834; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics