Category: pyrazoles-derivatives

Synthetic Route of 113808-86-9,Some common heterocyclic compound, 113808-86-9, name is 3,5-Dimethylpyrazole-4-carboxylic Acid, molecular formula is C6H8N2O2, 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 3,5-dimethyl-1H-pyrazole-4-carboxylic acid (18 mg, 0.13 mmol), HOBt*H2O (0.13 mmol), N-Methylmorpholine (1 mmol), 4-Dimethylaminopyridine (0.01 mmol) in 0.75 mL of DMF, a solution of intermediate 5 (0.11 mmol in 1 mL DMF) was added followed by EDC (neat, 0.13 mmol). The tube was closed with a screw cap and shaken over night at 40 C. 0.1 ml TFA was added and the volume was adjusted to 2.2 ml with DMF. The solution was filtered and submitted to preparative RP-HPLC purification to give 5-[4-(3,5-Dimethyl-1 H-pyrazole-4-carbonyl)-piperazin-1-ylmethyl]-thiophene-2-carboxylic acid (2-methoxy-pyridin-4-ylmethyl)-amide trifluoroacetate as a colorless film (33 mg, 52%). 1 H NMR (DMSO-d6, 500 MHz) d ppm 9.22 (t, 1 H), 8.1 (d, 1 H), 7.80 (d, 1 H), 7.30 (bs, 1 H), 6.90 (d, 1 H), 6.69 (s, 1 H), 4.6 (bs, 2H), 4.40 (bs, 2H), 4.3-3.7 (broad signal, 4H), 3.7 (s, 3H), 3.5-3.0 (broad signal, 4H), 2.13 (s, 6H). LC/MS (Method 3); Rt = 1.15 min; detected mass: m/z = 469.31 ([M+H]+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethylpyrazole-4-carboxylic Acid, its application will become more common.

Reference:
Patent; SANOFI; The designation of the inventor has not yet been filed; EP2881390; (2015); 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. 4027-57-0, name is Ethyl 5-methylpyrazole-3-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 5-methylpyrazole-3-carboxylate

Reference 4 Preparation of 3-formyl-5-methylpyrazole; Under nitrogen environment, 3-ethoxycarbonyl-5-methylpyrazole (1.0 g, 4.34 mmol) was dissolved in 15 ml of purified toluene, and DIBAL (8.68 ml, 8.62 mmol) was slowly added and stirred at -78C. The reaction progress and completion were confirmed using TLC (hexane : EtOAc = 6 : 1). Upon completion of the reaction, MeOH and water were slowly added to the reaction mixture and the resulting mixture was filtered through a celite bed, and the aqueous layer was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane : EtOAc : CH2Cl2 = 3 : 1 : 1) to obtain the title compound. Yield: 82.4% 1H NMR (300 MHz, CDCl3) delta 9.92 (s, 1H), 6.68 (s, 1H), 2.82 (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; Korea Institute of Science and Technology; EP1757590; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 70817-26-4, name is (1-Phenyl-1H-pyrazol-4-yl)methanol, 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. Recommanded Product: 70817-26-4

Example 14: (R)-3-(l-Phenyl-cycloheptanecarbonyloxy)-l-(l-phenyl-lH-pyrazol-4- ylmethyl)-l-azonia-bicyclo[2.2.2]octane chloridea) 4-Chloromethyl- 1 -phenyl- lH-pyrazole (1 -Phenyl- lH-pyrazol-4-yl)-methanol (2 g) in dichloromethane (15 mL) was treated with thionyl chloride (10 mL) and the mixture stirred at 200C for 1 h. The resulting suspension was diluted with z’s°hexane (15 mL) and the solid collected by filtration (1.12 g).1H NMR (399.826 MHz, DMSO-D6) delta 8.61 (s, IH), 7.84 – 7.80 (m, 3H), 7.53 – 7.47 (m, 2H), 7.35 – 7.30 (m, IH), 4.77 (s, 2H).

The synthetic route of (1-Phenyl-1H-pyrazol-4-yl)methanol has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ARGENTA DISCOVERY Ltd.; FORD, Rhonan; WO2009/139709; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 52773-23-6, These common heterocyclic compound, 52773-23-6, name is 1-(1,3-Dimethyl-1H-pyrazol-4-yl)ethanone, 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.

General procedure: To a solution of compound 1 (40 g, 258 mmol) in THF (480 ml)was added Et3N (39.3 ml, 283 mmol) and TMSOTf (51.3 ml,283 mmol) dropwise at 0 C over 1 h. The mixture was stirred atsame temperature for 1 h. To a reaction mixture was added NBS (50.5 g, 283 mmol) at 0 C over 10 min. The mixture was stirred at same temperature for 20 min. After quenching with water, the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered,and concentrated. To a solution of crude material in EtOH (600 ml) was added thiourea (19.61 g, 258 mmol) at room temperature.The mixture was refluxed for 1 h. After cooling to room temperature,EtOH was concentrated until about half volume. To are sulting mixture was added sat. NaHCO3 solution (500 ml) and H2O (300 ml) at room temperature. The mixture was stirred at same temperature for 30 min. The resulting solid was filtered and rinsed with H2O. The residue was purified by crystallization (EtOAc/hexane = 1/5) to afford 2 (49.9 g, 91.7%)

The synthetic route of 52773-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsuno, Naoki; Yukimasa, Akira; Yoshida, Osamu; Suzuki, Shinji; Nakai, Hiromi; Ogawa, Tomoyuki; Fujiu, Motohiro; Takaya, Kenji; Nozu, Azusa; Yamaguchi, Hiroki; Matsuda, Hidetoshi; Funaki, Satoko; Yamanada, Natsue; Tanimura, Miki; Nagamatsu, Daiki; Asaki, Toshiyuki; Horita, Narumi; Yamamoto, Miyuki; Hinata, Mikie; Soga, Masahiko; Imai, Masayuki; Morioka, Yasuhide; Kanemasa, Toshiyuki; Sakaguchi, Gaku; Iso, Yasuyoshi; Bioorganic and Medicinal Chemistry; vol. 25; 7; (2017); p. 2177 – 2190;,
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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. 86-92-0, name is 3-Methyl-1-p-tolyl-5-pyrazolone, A new synthetic method of this compound is introduced below., Computed Properties of C11H12N2O

General procedure: A mixture containing 4-fluorophenylhydrazine hydrochloride or 4-bromophenylhydrazinehydrochloride (4.47 mmol), ethyl acetoacetate (565 uL, 4.47 mmol) and 2.0mL of acetic acid was reflux for 8 h. The solution was then cooled to ambienttemperature and concentrated in vacuo. The crude product was purified by silica gelflash chromatography (PE/EA = 3/1, v/v) to afford 1-aryl-3-methyl-1H-pyrazol-5(4H)-one. Then 2.0 mmol 1-aryl-3-methyl-1H-pyrazol-5(4H)-one (R = 4-F, 4-Cl,4-Br, 4-CH3, 4-CH3O) was reacted with iodomethane (6 mmol) and acetonitrile (4 mL)in the dark in a sealed tube maintained at 120 in an oil bath. After 17 h, themixture was cooled to room temperature. The solvent was then evaporated in vacuo,and the resulted residue was purified by flash column chromatography (ethyl acetate)to yield 2t-2x.

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; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
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. 40704-11-8, name is 3-Methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Methyl-1H-pyrazole-4-carboxylic acid

Synthesis of /V-((2-hydroxy-4,( methyl-l-(l-benzrl)-l /-pyrazoie-4-carboxamide (Compound 11 esis 14] To a solution of 3-methyi-lH-pyrazole-4-carboxylic acid (1.26 g, 10 mmol) in methanol (100 mL) was added thionyl chloride (5.73 g, 45 mmol) at 0 C. The mixture was stirred for 12 hours. The solvent was evaporated in vacuo. To the residue, saturated sodium bicarbonate aqueous solution was added and the mixture was extracted with ethyl acetate (100 mLx 3), the organic phase was dried by sodium, sulfate. The mixture was filtered and the filtrate was concentrated in vacuo to give methyl 3-m.ethyl-lH~pyrazole~4~carboxylate (0.8 g, 57%). H NMR (300 MHz, CDCI3): delta 7.87 (s, 1H), 3.84 (s, 3H), 2.53 (s, 3H).

The synthetic route of 40704-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COOK, Andrew, S.; DAKIN, Les, A.; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-Christophe; NAVESCHUK, Christopher, G.; VASWANI, Rishi, G.; WO2013/120104; (2013); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 107862-65-7, 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 107862-65-7 as follows.

The bicyclic compound 16 (9mmol, 973mg) was dissolved in dry CHCl3 (40mL) and NBS (10mmol, 1.73g) was added. The bright red reaction mixture was stirred for 5min at room temperature. The mixture was diluted in CHCl3 (20mL), washed with water (3×50mL), dried over MgSO4, and concentrated in vacuo. The crude brown solid was dissolved in Et2O and filtered through a thin layer of silica gel. Evaporation of the solvent afforded a light yellow crystalline product (1.43g) in 77% yield (MP 82.6-84.0C) from 14. It became dark after standing at room temperature and at a lower temperature. Mp: 82.6-84.0C; 1H NMR: delta=7.43 (s, 1H, CH), 4.16 (t, 3J=7.3, 2H, NCH2), 2.82-2.87 (m, 2H, =C-CH2), 2.58-2.66 (m, 2H, NCH2CH2); 13C NMR: delta=144.8 (C), 143.9 (CH), 86.7 (C-Br), 49.0 (CH2), 26.2 (CH2), 22.6 (CH2); GC-MS m/z (%): 188 (M++1, 64), 186 (63), 107 (93), 80 (49), 51 (100); FTIR (KCl): 2962, 2922, 2854, 1706, 1641, 1452, 1318, 1226, 1156, 1013, 986. HRMS m/z calcdfor C6H8N2Br: 186.9871. Found: 186.9873.

According to the analysis of related databases, 107862-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Galeta, Juraj; Tenora, Luka?; Man, Stanislav; Pota?ek, Milan; Tetrahedron; vol. 69; 34; (2013); p. 7139 – 7146;,
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. 4331-28-6, name is 1H-Pyrazol-4-amine hydrochloride belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H6ClN3

2-(Methoxy(phenyl)methyl)-6-(methylcarbamoyl)isonicotinic acid (150 mg, 0.50 mmol) was added to a dry flask. DMF (2 mL) was added, followed by HATU (228 mg, 0.60 mmol) and 1H-pyrazol-4-amine, hydrochloride (59.7 mg, 0.50 mmol). The reaction was stirred for 2 mm and then DIPEA (0.262 mL,1.498 mmol) was added. The reaction was stirred at rt for 30 mm. The reaction mixture was added directly to 3 x LCMS vials, diluting with DMS0/Me0H and purified by 3 x MDAP (High pH). Theappropriate fractions were concentrated in vacuoto afford the desired product as a yellow solid – (+1- )-6-(methoxy(phenyl)methyl)-N2-methyl-N4-( 1 H-pyrazol-4-yl)pyridine-2,4-dicarboxamide (100 mg, 0.27 mmol, 55 % yield)LCMS (2 mm Formic): Rt = 0.82 mi [MH]+ = 366.3.1H NMR (400 MHz, DMS0-d6) O ppm 12.69 (br. s., 1 H) 10.92 (5, 1 H), 8.67 (q, J=4.8 Hz, 1H), 8.45 (d, J=1.7 Hz, 1 H), 8.17 (d, J=1.5 Hz, 1 H), 8.04 (br. 5., 1 H), 7.72 (br. 5., 1 H), 7.51 (d, J=7.1 Hz, 2 H), 7.36 (t, J=7.5 Hz, 2 H), 7.24 – 7.31 (m, 1 H), 5.52 (5, 1 H), 3.39 (5, 3 H), 2.88 (d, J=4.9 Hz, 3 H)

The synthetic route of 4331-28-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (N.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan, Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (0 pag.)WO2018/158210; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 873191-23-2, 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. 873191-23-2, name is 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

71 a) To a stirring solution of (2,5-dimethyl-2H-pyrazol-3-yl)-methanol (100 mg, 0.79 mmol) in diethyl ether (3 mL) is added PBr3 (25 muL, 0.26 mmol). The reaction is stirred at room temperature for 18 hours, then water is added. The diethyl ether layer is separated and stored over solid NaOH and used in Step 71 b without further characterization. 71b) BEMP (137 pL, 0.47 mmol) is added to a solution of (2-methyl-1H-pyrrolo[2,3- b]pyridin-3-yl)-acetic acid methyl ester (60 mg, 0.29 mmol) in DMF (0.8 mL). After 35 minutes, the diethyl ether layer from Step 71 a (1.8 mL) is added. After 3 days, the reaction is partitioned between water and 1:1 EtOAc/ether. The organic layer is washed with brine then evaporated. The residue is purified by flash column chromatography (49:1 EtOAc/MeOH elution) to furnish [1-(2,5-dimethyl-2H-pyrazol-3-ylmethyl)-2-methyl-1H- pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester; MH+ = 313.

The synthetic route of 5-(Bromomethyl)-1,3-dimethyl-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/123731; (2005); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 128694-63-3,Some common heterocyclic compound, 128694-63-3, name is 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, molecular formula is C6H5F3N2O2, 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.

A mixture of 0.19 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid, 0.15 g of thionyl chloride and 5 mL of hexane was heated to reflux for 2 hours. The reaction mixture was concentrated under reduced pressure to obtain 0.14 g of 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride. To a mixture of 0.22 g of N-(2-aminobenzoyl)-N’-ethoxycarbonylhydrazine and 10 mL of pyridine was added 0.14 g of the resulting 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carbonyl chloride, and the mixture was stirred at room temperature for 2 hours. Water was poured into the reaction mixture, and a formed precipitate was collected by filtration to obtain 0.23 g of a compound I-(3). 1H-NMR (DMSO-d6, TMS) delta (ppm): 1.20 (3H, t, J=8 Hz), 4.10 (2H, q, J=8 Hz), 4.19 (3H, s), 7.17 (1H, s), 7.28 (1H, t, J=8 Hz), 7.60 (1H, t, J=8 Hz), 7.79 (1H, d, J=8 Hz), 8.37 (1H, d, J=8 Hz), 9.02 (1H, brs), 10.41 (1H, brs), 11.50 (1H, brs)

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

Reference:
Patent; Natsuhara, Katsuya; Nishimura, Shinya; US2010/137314; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics