Tag: M.W:200-300

Some common heterocyclic compound, 83-10-3, name is 1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid, molecular formula is C12H12N2O3, 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. category: pyrazoles-derivatives

Step 5) N-(4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide To a solution of 1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol (3.75 g, 11.6 mmol) in DCM (31 mL) was added 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (2.7 g, 11.8 mmol), HOAT (0.32 g, 2.32 mmol), EDCI (2.7 g, 13.9 mmol). The reaction mixture was refluxed for 3 hours, then cooled to 45 C. and continued to stir for 4 hours. Additional EDCI (0.4 eq., 0.90 g, 4.64 mmol) was added and the reaction was stirred overnight at 45 C. The mixture was cooled to room temperature and diluted with a mixture of EtOAc (30 mL) and water (30 mL). After stirring at room temperature for 2 hours, the mixture was filtered. The solid was stirred in 95% EtOH (15 mL) at -5 C. for 5 hours. The solid was collected through filtration, dried in vacuo at 50 C. overnight to give the title compound as a gray-white solid (3.04 g, 48.87%). MS (ESI, pos. ion) m/z: 539.2 [M+1]; 1H NMR (400 MHz, CDCl3): delta 1.40 (s, 6H), 2.80 (s, 3H), 3.36 (s, 3H), 3.97 (s, 2H), 6.45-6.46 (d, J=5.2 Hz, 1H), 7.11-7.13 (d, J=8.56 Hz, 2H), 7.36-7.39 (m, 3H), 7.47-7.49 (d, J=6.8 Hz, 1H), 7.54-7.58 (m, 2H), 7.74-7.76 (d, J=8.4 Hz, 2H), 8.25-8.27 (d, J=9.04 Hz, 1H), 8.56-8.57 (d, J=5.08 Hz, 1H). 13C NMR (100 MHz, DMSO-d6): delta 11.46, 26.63, 33.31, 48.62, 68.63, 76.24, 97.04, 108.13, 119.04, 120.75, 121.56, 122.81, 127.19, 128.91, 129.51, 133.02, 136.46, 148.93, 151.82, 153.75, 160.37, 161.18, 161.24, 163.05.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 83-10-3, its application will become more common.

Reference:
Patent; XI, Dr. Ning; US2012/219522; (2012); 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. 138907-68-3, name is Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate

Intermediate 9; 5-Amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxyliotac acid; To a suspension of ethyl 5-amiotano-1-(4-fluorophenyl)-1 /-/-pyrazole-4-carboxylate (12 1g, 48 5mmol) in ethanol (250ml) was added a solution of lithium hydroxide (5 8g, 242mmol) in water (100ml) The mixture was stirred at reflux for 2 5 hours It was allowed to cool and concentrated to 50% of its volume before 5M hydrochloric acid (47ml) was added. After stirring for 15 minutes, the resulting white solid was filtered off and further 5M hydrochloric acid (3ml) was added to the filtrate and the resulting solid was filtered and the combined solids were washed with water and diethyl ether and then dried under vacuum to give the title compound (10.27g).1H NMR (400 MHz, DMSOd6) delta ppm 12.09 (br. s., 1 H) 7.67 (s, 1 H) 7.54 – 7.60 (m, 2H) 7.34 – 7.41 (m, 2H) 6.29 (br. s., 2H). LC-MS Retention Time 2.20mins, MH+ 222.

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; GLAXO GROUP LIMITED; WO2008/777; (2008); 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. 141573-95-7, name is Ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate, A new synthetic method of this compound is introduced below., Formula: C8H10F2N2O2

ethyl 5-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate containing 0.2 area%, Purity 96.6 area% of ethyl 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylate 10.0 g (0.05 mol), toluene 94 g, water 15.2 g, 25 wt% sodium hydroxide aqueous solution 1.8 g (0.07 mol) were added to the 200ml round-bottomed flask, while stirring it was heated in an oil bath and reacted under reflux for 23 hours. After cooling to room temperature, 15 mass% hydrochloric acid 21.0 g (0.09 mol) was dropped from the dropping funnel. After dropping, after cooling for 1 hour in an ice-water bath, using a 5C filter paper, suction filtered through a Kiriyama funnel, the filtrate was washed with 2 volumes of cold water. The obtained filtrate was dried under reduced pressure at 80 C. for 4 hours and got 8.60 g of crystals. When this crystal was analyzed by HPLC, it was 3- (difluoromethyl) -1-methyl -1H- pyrazole-4-carboxylic acid : 99.2 area %, 5- (difluoromethyl) -1-methyl-1 H-pyrazole-4-carboxylic acid : 0.1 area %. The toluene layer obtained by separating the filtrate into two layers, after concentrated in an evaporator, dried under reduced pressure at 80 C for 4 hours, got 0.02 g of crystals. When this crystal analyzed by HPLC, it was 3- (difluoromethyl) -1-methyl -1H- pyrazole-4-carboxylic acid : 27.2 area %, 5- (difluoromethyl) -1-methyl-1 H-pyrazole-4- carboxylic acid: 15.0 area %.

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; CENTRAL GLASS COMPANY LIMITED; IMURA, HIDEAKI; TAKADA, NAOTO; (11 pag.)JP5830957; (2015); B2;,
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. 92525-10-5, name is 3-Iodo-1-methyl-1H-pyrazole, A new synthetic method of this compound is introduced below., COA of Formula: C4H5IN2

A degassed solution of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpyridin-2(1H)-one (27 mg, 0.100 mmol), 3-iodo-1-methyl-1H-pyrazole (20 mg, 0.097 mmol), N1,N2-dimethylethane-1,2-diamine (5 mg, 0.049 mmol), copper iodide (4 mg, 0.020 mmol), and potassium phosphate (43 mg, 0.197 mmol) 2 mL of N-methylpyrrolidone was heated to 70 C. After allowing the reaction to stir overnight (17 h) at 70 C., the reaction was complete and allowed to cool to room temperature. The reaction was extracted 3X’s with EtOAc (3*5 mL) and 2X’s with NaHCO3 (3*10 mL). The crude organic layers were combined, dried over anhydrous Na2SO4 (s), filtered and then concentrated in vacuo. The crude mixture was then purified using the ISCO flash chromatography system using a 0-100% EtOAc/100-0% Hexane gradient mixture. A second column was done on the impure product using a gradient of MeOH/CHCl3 after which, the appropriate fractions were concentrated, to afford a yellow solid (17 mg, 52%). 1H NMR (DMSO) delta: 8.01 (s, 1H), 7.79 (d, J=6.0, 1H), 6.34 (d, J=6.0, 1H), 6.24 (m, 1H), 6.15 (d, J=7.0 Hz, 2H), 4.00 (br. S, 2H), 3.22 (s, 2H), 2.64 (t, j=5.3 Hz, 2H), 2.20 (s, 3H)

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; Allergan, Inc.; Wurster, Julie; Yee, Richard; Hull III, Clarence Eugene; Malone, Thomas C.; (39 pag.)US2016/96832; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-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. HPLC of Formula: C10H9IN2

General procedure: To iodopyrazole (1 mmol) dissolved in THF (10 mL), Fuajasite (250 mg) was added. Nitric acid (d 1.52 g/cm3, 10 mL) was added slowly and the mixture was stirred at room temperature for required time. The catalyst was recovered by filtration and the filtrate was extracted repeatedly with dichloromethane. The solvent was removed under vacuum to obtain nitropyrazole.

The synthetic route of 1-Benzyl-4-iodo-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ravi; Tewari, Surya P.; Catalysis Communications; vol. 42; (2013); p. 35 – 39;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15802-75-2, name is 4-Iodo-3-methyl-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 15802-75-2, COA of Formula: C4H5IN2

Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol3, 6-diiodetetrazine,2.2 mmol 3-methyl-4-iodopyrazole, 0.03 mmol palladium acetate, 0.06 mmol(3′-dimethoxy-2 ‘, 4′, 6′-triisopropyl (1,1′-biphenyl) -2-yl) phosphine, 5.0 mmol of sodium tert-butoxide And 5 ml of toluene, the reaction tube was purged with nitrogen three times and then heated to 110 C with an oil bath under magnetic stirring,The reaction was refluxed for 18 hours. To the room temperature; the reaction solution was further added, 8.0 mmol of 3,5-dicarboxyphenylboronic acid,0.03 mmol palladium acetate, 0.06 mmol 2′-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1,1’-biphenyl sodium salt,12.0 mmol of cesium carbonate, and 200 mmol of water; and then heated to 100 C with an oil bath under magnetic stirring,The reaction was refluxed for 48 hours. Down to room temperature; add 20 ml of water, filtration, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1,After stirring at room temperature for 6 h, the mixture was filtered, washed with ethanol and dried to give product 8 with a yield of 76%.The mass spectrum (ESI) of the product (C26H18N8O8) was 570.12.

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

Reference:
Patent; Luoyang Normal College; Li Hongmei; Xu Chen; Wang Zhiqiang; Tu Tianyong; Hao Xinqi; (10 pag.)CN106674208; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 345637-71-0,Some common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, 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.

Solution A: To a solution of [5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetic acid (0.7 g) in dichloromethane (20 ml) at room temperature were added one drop of Nu,Nu-dimethylformamide and, dropwise, oxalyl chloride (0.8 ml). After stirring at room temperature for 2 hours, the solvent was removed and the residue was dissolved again in dichloromethane (10 ml) (solution A).To a solution of l-(2-{3-[2-(piperidin-4-yl)-l,3-thiazol-4-yl]-4,5-dihydro-l,2-oxazol-5- yl}phenyl)ethanone hydrochloride (1.20 g) in dichloromethane (20 ml) was added, at room temperature, diisopropylethylamine (1.60 ml). After 15 minutes, solution A was added dropwise. After stirring at room temperature overnight, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave l-(4-{4-[5-(2-acetylphenyl)-4,5-dihydro-l,2- oxazol-3 -yl] – 1 ,3 -thiazol-2-yl}piperidin- 1 -yl)-2- [5 -methyl-3 -(trifluoromethyl)- lH-pyrazol- 1 -yl] ethanone (1.04 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; TSUCHIYA, Tomoki; WASNAIRE, Pierre; HOFFMANN, Sebastian; CRISTAU, Pierre; SEITZ, Thomas; KLUTH, Joachim; HILLEBRAND, Stefan; BENTING, Juergen; PORTZ, Daniela; WACHENDORFF-NEUMANN, Ulrike; WO2012/25557; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 51516-70-2,Some common heterocyclic compound, 51516-70-2, name is 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, molecular formula is C10H7FN4, 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 theintermediate compounds 2 (1 mmol) and 3 (1 mmol) in ethanol(10 mL) was stirred at reflux for 2 h. After cooling to roomtemperature, the precipitated solid was filtered, and thenrecrystallized from ethanol to give the title compounds 5a-5p.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Article; Lv, Xian-Hai; Ren, Zi-Li; Li, Dong-Dong; Ruan, Ban-Feng; Li, Qing-Shan; Chu, Ming-Jie; Ai, Cheng-Ying; Liu, Dao-Hong; Mo, Kai; Cao, Hai-Qun; Chinese Chemical Letters; vol. 28; 2; (2017); p. 377 – 382;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 10250-64-3, name is 1-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acid, molecular formula is C11H10N2O2, 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. Computed Properties of C11H10N2O2

To a stirred suspension of 1-methyl-3-phenyl-1H-pyrazole-5-carboxylic acid (46 mg, CAS 10250-64-3) in dichloroethane (2 ml) were added oxalyl chloride (44 mul) and DMF (2 drops). The reaction mixture was stirred at room temperature for 1 h and was then concentrated in vacuo. The residue was dissolved in THF (1 ml) and the resulting solution was added dropwise to a stirred solution of (+)-(R)-2-(4-amino-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (50 mg, example 1h) and triethylamine (118 mul) in THF (2 ml). The reaction mixture was stirred at room temperature for 2 h. The crude reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: 0% to 50% EtOAc in heptane) to give (R)-2-{3-fluoro-4-[(2-methyl-5-phenyl-2H-pyrazole-3 carbonyl)-amino]-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (81 mg, quant.) as a white solid. MS (ISP): 503.1 ([M+Na]+), 481.3 ([M+H]+), 425.2 ([M+H-C4H8]+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10250-64-3, its application will become more common.

Reference:
Patent; Galley, Guido; Norcross, Roger; Pflieger, Philippe; US2012/316165; (2012); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 155377-19-8, A common heterocyclic compound, 155377-19-8, name is Ethyl 3-(trifluoromethyl)pyrazole-4-carboxylate, molecular formula is C7H7F3N2O2, 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.

According to the procedure of Buchwald et al . (J. Org. Chem. 2004, 69, 5578), to a 50 mL sealed tube flushed with argon were added copper (I) iodide (0.02288 g, 0.1201 mmol) , K2CO3 (0.6972 g, 5.045 mmol), and ethyl 3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.500 g, 2.402 mmol). ( IS, 2S) -N1,N2- Dimethylcyclohexane-1, 2-diamine (0.06834 g, 0.4805 mmol) and 2-bromophenol (0.3343 mL, 2.883 mmol) were then added along with 3 mL of toluene (degassed under argon) . The tube was sealed and heated to 1100C overnight, then cooled to room temperature and the mixture was filtered through celite to remove the solid. The filtrate was concentrated under vacuum and the residue was purified by chromatography (10% ether/DCM) to give ethyl 1- (2-hydroxyphenyl) -3- (trifluoromethyl) -IH- pyrazole-4-carboxylate (0.660 g, 91%) as a solid: 1H NMR (400 MHz, CDCl3) delta 1-40 (t, 3H, J = 7.0 Hz), 4.39 (q, 2H, J = 7.0 Hz), 7.00 (m, IH), 7.16 (m, IH), 7.31 (m, IH), 7.42 (m, .1H), 8.56 (m, IH).

The synthetic route of 155377-19-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11130; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics