Category: pyrazoles-derivatives

Reference of 129768-28-1,Some common heterocyclic compound, 129768-28-1, name is 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid, molecular formula is C5H3F3N2O2, 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 73SYNTHESIS OF N-(2-CHLOROBENZYL)-N-(2-( 1,1 -DIOXIDOTETRAHYDROTHIOPHEN-3 -YL)ETHYL)-3-(TRIFLUOROMETHYL)- 1H-PYRAz0LE-5-cARB0xAMIDE. To a solution of 3-trifluoro-1H-pyrazole-5-carboxylic acid (0.248 g, 1.377 mmol) and N-(2-chlorobenzyl)-2-(tetrahydro-2H-thiopyran-4-yl)ethanamine (0.372 g, 1.377 mmol) in ACN (5 mL) was added T3P (Propylphosphonic anhydride solution, 50 wt% in ethyl acetate) (0.460 g, 1.466 mmol) and TEA (0.495 g). Then the reaction mixture was stirred at r.t. for 1 day. The resulting reaction mixture was diluted with 30 mL DCM and washed with water 10 mL. The DCM phase was dried with Na2SO4 and evaporated. Preparative HPLC purification provided pure product N-(2- chlorobenzyl)-N-(2-(tetrahydro-2H-thiopyran-4-yl)ethyl)-3 -(trifluoromethyl)- 1 Hpyrazole-5-carboxamide (0.060 g, 0.139 mmol, 10% yield).?H-NMR (Acetone-d6/400 MHz): 7.41 (m, 4H), 6.80 (m, 1H), 4.95 (d, 2H), 3.61 (d, 2H), 2.60 (m, 4H), 1.99 (m, 1H), 1.61 (m, 2H), 1.30 (m, 4H). MS (ES, mlz): 432.4 (M+1, 100.0).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethyl)-1H-pyrazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; HO, Koc-Kan; XU, Yong; SAUNDERS, Micheal, David; LIU, Xiaohui; PEARCE, Scott, Albert; WRIGHT, Kevin, Bret; FOULKS, Jason, Marc; PARNELL, Kenneth, Mark; KANNER, Steven, Brian; VOLLMER, David, Lee; LIU, Jihua; WO2014/62838; (2014); A2;,
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. 288148-34-5, name is 1-Methyl-1H-pyrazole-4-sulfonyl chloride, A new synthetic method of this compound is introduced below., category: pyrazoles-derivatives

General procedure: A mixture of the appropriate (aryloxy)ethyl piperidine(0.38 mmol) in CH2Cl2 (3 mL), and TEA (1.14 mmol) was cooled down (ice bath), and arylsulfonyl chloride (0.46 mmol) was added at 0 C in one portion. The reaction mixture was stirred for 2-6 h under cooling. Then, the solvent was evaporated and the sulfonamides were purified using silica gel column with CH2Cl2/MeOH as an eluting system. Free bases were then converted into the hydrochloride salts by treatment of their solution in anhydrous ethanol with 1.25 M HCl in MeOH.; 9.2.6.16 1-Methyl-N-{1-[2-(2-(t-butyl)phenoxy)ethyl]piperidin-4-yl}-N-cyclopropylmethyl-1H-pyrazole-4-sulfonamide (31) Yellow oil, 110 mg following chromatographic purification over silica gel with CH2Cl2/MeOH (9:0.5); LC/MS purity 100%, tR = 6.24, C25H38N4O3S, MW 474.66, Monoisotopic Mass 474.27, [M+H]+ 475.2 1H NMR (300 MHz, CDCl3) delta 0.25-0.31 (m, 2H), 0.51-0.57 (m, 2H), 1.38 (s, 9H), 1.56-1.63 (m, 2H), 1.74-1.89 (m, 2H), 2.18-2.21 (m, 3H), 2.84 (t, J = 5.92 Hz, 2H), 3.03 (d, J = 11.55 Hz, 2H), 3.10 (d, J = 6.76 Hz, 2H), 3.61-3.64 (m, 1H), 3.91 (s, 3H), 4.12 (t, J = 5.95 Hz, 2H), 6.88 (qd, J = 7.73, 0.98 Hz, 2H), 7.14 (td, J = 7.72, 1.68 Hz, 1H), 7.24-7.29 (m, 1H), 7.66-7.70 (m, 1H), 7.78 (s, 1H). 13C NMR (75 MHz, CDCl3) delta 5.12, 12.47, 29.69, 29.80, 30.01, 30.77, 34.81, 48.31, 53.79, 55.84, 57.08, 65.81, 112.03, 115.99, 116.28, 120.44, 126.66, 126.99, 129.42, 129.54, 138.09, 157.46, 163.05, 166.41. Anal. calcd for C25H38N4O3S·HCl: C, 58.75; H, 7.69; N, 10.96; S, 6.27; Found: C, 58.94; H, 7.79; N, 10.72; S, 6.16. Mp for C25H38N4O3S·HCl: 193.7-194.5 C.

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:
Article; Canale, Vittorio; Kurczab, Rafa?; Partyka, Anna; Sata?a, Grzegorz; S?oczy?ska, Karolina; Kos, Tomasz; Jastrz?bska-Wi?sek, Magdalena; Siwek, Agata; P?kala, Elzbieta; Bojarski, Andrzej J.; Weso?owska, Anna; Popik, Piotr; Zajdel, Pawe?; Bioorganic and Medicinal Chemistry; vol. 24; 2; (2016); p. 130 – 139;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 155377-19-8, name is Ethyl 3-(trifluoromethyl)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 155377-19-8, Recommanded Product: Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate

(R)-lambda/-(5-(hydroxymethyl)-2,3-dihydro-1 H-inden-2-yl)propane-2-sulfonamide (2.82 mmol, 760 mg) was dissolved in DCM (20 mL) and Thionyl Chloride (5.64 mmol, 0.409 mL, 671 mg) added and the solution stirred at room temperature. After 45 min the mixture was concentrated then azeotroped with DCM (4 x 10 mL) to give a yellow oil. To this oil was added DMF (10 mL) and potassium carbonate (8.46 mmol, 1170 mg) followed by ethyl 3- (trifluoromethyl)-1 H-pyrazole-4-carboxylate (2.82 mmol, 587 mg) . The mixture was heated to 60 0C with stirring for 1 h. The reaction was concentrated to remove DMF before partitioning between EtOAc/Water. The phases were mixed and separated and the aqueous phase further washed with EtOAc (x 2). Combined organics were dried and concentrated to give a light yellow oil which was purified on silica eluting with 25% EtOAc/heptane. Desired fractions were collected and concentrated to give (R)-ethyl 1-((2- (1-methylethylsulfonamido)-2,3-dihydro-‘//-/-inden-5-yl)methyl)-3-(trifluoromethyl)- 1H- pyrazole-4-carboxylate as a colourless solid (1.1 1 g, 86 %).1H NMR (400 MHz, CDCI3) delta 1.31 (t, 3H) 1.39 (d, 6H) 2.9 (m, 2H) 3.17 (sept, 1 H) 3.30 (m, 2H) 4.30 (m, 4H) 5.28 (s, 2H) 7.13 (m, 2H) 7.25 (d, 1 H) 7.89 (s, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; N.V. ORGANON; WO2009/147167; (2009); 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. 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Cyclopropyl-1H-pyrazol-3-amine

101B. 2-Chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrrolo[1,2-f][1,2,4]triazine-7-carbaldehyde A mixture of 101A (371 mg, 1.72 mmole), 5-cyclopropyl-1H-pyrazol-3-amine (139 mg, 1 equiv), and diisopropylethylamine (0.51 mL, 1.7 equiv) in isopropyl alcohol (1.7 mL) was stirred at RT overnight. The reaction was diluted with a mixture of dichloromethane_methanol=9:1, washed with water and dried (Na2SO4). Removal of the solvents followed by radial silica gel chromatography (step gradient elution with mixtures of dichloromethane containing 0 to 7.5% methanol) afforded the product as a solid (279 mg, 54% yield): MS: 303 (M+H)+; HPLC Ret Time: 2.61 min (Phenomenex-Luna S10 3.0*50 mm column, 3 min gradient, 4 mL/min).

The synthetic route of 175137-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/9497; (2008); 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. 330792-70-6, name is 3-Amino-5-(4-phenoxyphenyl)pyrazole-4-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 330792-70-6

To a solution of I-9 (1.50 g, 5.4 mmol) in DMF (20 mL) is added sodium hydride (60percent dispersion in mineral oil, 0.26 g, 6.5 mmol). The mixture is stirred for 5 min then I-1 (2.39 g, 6.5 mmol) is added. The mixture is heated at 70° C. for 18 h then cooled to ambient temperature. The mixture is partitioned between EtOAc and water then organics are collected, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, Hep to 70percent EtOAc in Hep) to afford I-53 (1.2 g, 47percent) m/z 472.2 [M+H].

According to the analysis of related databases, 330792-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BENTZIEN, Joerg Martin; BERRY, Angela Kay; BOSANAC, Todd; BURKE, Michael Jason; DISALVO, Darren Todd; HORAN, Joshua Courtney; LIANG, Shuang; MAO, Can; MAO, Wang; SHEN, Yue; SOLEYMANZADEH, Fariba; ZINDELL, Renee M.; US2014/45813; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 13808-64-5, A common heterocyclic compound, 13808-64-5, name is 4-Bromo-3-methylpyrazole, molecular formula is C4H5BrN2, 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.

Compound 11 is prepared from compound 10 by reacting (1 eq), Boc2O (1.5 eq), Na2CO3 (2 eq) in DCM at RT for 16 h. After work up and the NMR showed characteristic peaks and was used as such for the next step. In subsequent step compound II (1 eq), and 12 (1.1 eq) in presence of PdCl2(dppf) (0.05 eq), KOAc (3 eq), DMSO was heated to 90 C., 16 h. After column purification LCMS showed 50% of desired mass of compound 11. Key intermediate 14 was prepared was prepared by reacting (1 eq), BH3-DMS (3 eq), THF, RT, 16 h. After work up LCMS showed 96% purity of the compound 14.

The synthetic route of 13808-64-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BETA CAT PHARMACEUTICALS, LLC; Vankayalapati, Hariprasad M.; Horrigan, Stephen; US2013/123281; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1190380-49-4, The chemical industry reduces the impact on the environment during synthesis 1190380-49-4, name is 1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, I believe this compound will play a more active role in future production and life.

General procedure: General Procedure 35To the appropriate 1H-pyrrole-2-carboxylic acid (1 mol equiv.) in DCM (10 mL/mmol of carboxylic acid) were added triethylamine (2.5 mol equiv.), 2-chloro-1-methylpyridinium iodide (1.1 mol equiv.) and the appropriate amine (1.25 mol equiv.). The resulting solution was stirred at 42 C for 24 h. Upon completion, the solvent was removed in vacuo. The crude residue was dissolved in EtOAc (30 mL), washed with saturated aq. NaHCO3 (20 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography.

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-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; REUILLON, Tristan; MILLER, Duncan; MYERS, Stephanie; MOLYNEUX, Lauren; CANO, Celine; HARDCASTLE, Ian; RIGOREAU, Laurent; GOLDING, Bernard; NOBLE, Martin; (246 pag.)WO2016/42341; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 500011-84-7,Some common heterocyclic compound, 500011-84-7, name is 3-Bromo-1-(dimethylsulfamoyl)pyrazole, molecular formula is C5H8BrN3O2S, 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 trifluoroacetic acid (70 mL) was slowly added [3-BROMO-N, N-DIMETHYL-LH-] [PYRAZOLE-1-SULFONAMIDE] (i. e. the bromopyrazole product of Step A) (57.04 g). The reaction mixture was stirred at room temperature for 30 minutes and then concentrated at reduced pressure. The residue was taken up in hexane, insoluble solids were filtered off, and the hexane was evaporated to afford the crude product as an oil. The crude product was further purified by chromatography on silica gel using ethyl [ACETATE/DICHLOROMETHANE] (10: 90) as eluent to afford an oil. The oil was taken up in dichloromethane, neutralized with aqueous sodium bicarbonate solution, extracted with methylene chloride (3x), dried over magnesium sulfate and concentrated to afford the title product as a white solid (25.9 g), m. p. [61-64 C.] [1H] NMR (CDC13) [8] 6.37 (d, 1H), 7.59 (d, 1H), 12.4 (br s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-1-(dimethylsulfamoyl)pyrazole, its application will become more common.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; STEVENSON, Thomas, Martin; WO2003/106427; (2003); A2;,
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. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 1H-Pyrazole-4-carbonitrile

To a suspension of K2CO3 (63 mg, 0.46 mmol) in THF (10 mL) was added 4-cyanopyrazole (43 mg, 0.46 mmol) and compound SB-W (100 mg, 0.23 mmol). After stirring at room temperature for 15h, the reaction mixture was poured into 5 mL H20 and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine (2 x 10 mL), dried over sodium sulfate,filtered and concentrated under vacuum. The residue was purified by reverse-phase prep-HPLC to afford SB-9 as a white solid (43.5 mg, 0.095 mmol, 41.7%). 1HNMR (500 MHz, CDC13) delta (ppm7.86 (IH, s), 7.82 (IH, s), 5.01 (IH, AB), 4.91 (IH, AB), 3.53 (2H, q), 3.22 (2H, s), 2.61 (IH, t), 0.67 (3H, s), 0.67-2.25 (24H, m). LCMS: Rt = 2.37 mm. m/z = 454.4 [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; SAGE THERAPEUTICS, INC.; BOTELLA, Gabriel Martinez; HARRISON, Boyd L.; ROBICHAUD, Albert Jean; SALITURO, Francesco G.; BERESIS, Richard Thomas; WO2014/169833; (2014); 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. 75415-03-1, name is 2-(1H-Pyrazol-3-yl)pyridine, A new synthetic method of this compound is introduced below., Formula: C8H7N3

[Mn(m2-O)(H2O)2(HL)]2n2nNIPH (2): A mixture of Mn(OAc)24H2O (0.10 g, 0.4 mmol), H2NIPH (0.084 g, 0.4 mmol), L (0.058 g, 0.4 mmol), and 18 mL H2O was placed in a Teflon reactor (30 mL) and the pH value was adjusted to about 7 with 0.5 mol/L NaOH solution. Then the mixture was heated at 140C for 7 days. After cooling to room temperature at a rate of 10C/h, brown crystals of 1 were collected in 45% yield. Anal. Calcd. for C32H30Mn2N8O18 (%): C, 41.57; H, 3.27; N, 12.12. Found (%): 41.36; H, 3.01; N, 11.98. IR (KBr, cm-1): 3413(m), 3102(w), 1630(s), 1606(s), 1583(m), 1533(m), 1495(w), 1443(w), 1334(s), 1101(w), 998(w), 788(w), 720(m), 537(w).

The synthetic route of 75415-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Zhi-Tao; Valtchev, Valentin; Fang, Qian-Rong; Li, Xiu-Mei; Pan, Ya-Ru; Inorganic and Nano-Metal Chemistry; vol. 49; 2; (2019); p. 44 – 50;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics