Category: pyrazoles-derivatives

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. 175137-46-9, name is 5-Cyclopropyl-1H-pyrazol-3-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H9N3

Referential Example 5 2-Chloro-N-(5-cyclopropyl-lH-pyrazol-3-yl)-6-methylpyrimidin-4-amine (189) A mixture of 5-cyclopropyl-lH-pyrazol-3 -amine (1.98 g, 16.07 mmol), 2,4-dichloro-6-methyl-pyrimidine (2.62 g, 16.07 mmol), DIPEA (5.7 mL, 32.15 mmol) and anhydrous EtOH (50 mL) was stirred at 70 oC under N2 for 3 d. The reaction mixture was cooled and poured into water (ca. 700 mL). The reaction was stirred at RT overnight until solid precipitated out. The solid was filtered, washed with additional water and pumped dry under high- vacuum to afford 2.37 g (59%) of 189 as a solid: 1H NMR (400 MHz, DMSO-i/6) delta 12.12 (s, 1H), 10.08 (s, 1H), 7.04 (br s, 1H), 5.93 (br s, 1H), 2.27 (s, 3H), 1.93 to 1.84 (m, 1H), 0.96 – 0.88 (m, 2H), 0.70 – 0.64 (m, 2H).

According to the analysis of related databases, 175137-46-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; ALIAGAS-MARTIN, Ignacio; CRAWFORD, James; LEE, Wendy; MATHIEU, Simon; RUDOLPH, Joachim; WO2013/26914; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 176969-34-9, A common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
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. 35344-95-7, name is 1H-Pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H4N2O

tert-Butyl 3-[(methylsulfonyl)oxy]-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate was reacted with 1H-pyrazole-4-carbaldehyde and cesium carbonate to afford tert-butyl 3-(4-formyl-1H-pyrazol-1-yl)-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate. This material was treated with (diethylamino)sulfur trifluoride to provide the requisite tert-butyl 3-[4-(difluoromethyl)-1H-pyrazol-1-yl]-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

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 35344-95-7.

Reference:
Patent; PFIZER INC.; BRODNEY, MICHAEL AARON; BUTLER, CHRISTOPHER RYAN; MCALLISTER, LAURA ANN; HELAL, CHRISTOPHER JOHN; O’NEIL, STEVEN VICTOR; VERHOEST, PATRICK ROBERT; (103 pag.)US2018/208607; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 37687-18-6, 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 37687-18-6 as follows.

1-(1-Methyl-1H-pyrazol-4-yl)ethanone (18 g, 145 mmol) and NBS (31 g, 174 mmol) were added to the reaction flask.Add CCl4 (80 mL) to dissolve, and add AIBN (2.4 g, 14.5 mmol) in portions under reflux, and react under 365 nm UV irradiation for 24 h.After the reaction is completed, the system is poured into ice water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent is removed for column chromatography.(eluent: Petroleum ether/EtOAc (v/v) = 5/1),5.9 g of a yellow oily product were obtained in a yield: 20%.

According to the analysis of related databases, 37687-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dongguan Dongyang Guang Ke Research And Development Co., Ltd.; Li Yitao; Lin Jian; Chi Weilin; Zeng Shuiming; (43 pag.)CN110294747; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 37622-90-5, 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 37622-90-5 as follows.

To an oven dried, 100 mL round bottom flask was added ethyl 1H-pyrazole-4-carboxylate (3.2 g, 22.8 mmol), Cs2CO3 (8.9 g, 27.4 mmol), 20 mL DMF and ethyl iodide (2 mL, 23.9 mmol). The reaction was stirred for 50 C. for 12 h. 20 mL water was added and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (1×20 mL), brine and dried with Na2SO4 to afford 3.6 grams of ethyl 1-ethyl-1H-pyrazole-4-carboxylate as an oil.

According to the analysis of related databases, 37622-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.)US2015/376136; (2015); 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. 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H6N2O2

To a solution of 4-bromoaniline (200 mg, 1.16 mmol, 1 eq) in EtOAc (5 mL) was added 2-methylpyrazole-3-carboxylic acid (175.95 mg, 1.40 mmol, 1.2 eq), DIEA (450.78 mg, 3.49 mmol, 607.52 muL, 3 eq) and T3P (2.22 g, 3.49 mmol, 2.07 mL, 3 eq). The mixture was stirred at 60 C. for 12 h. Sat. NaHCO3 solution (10 mL) was added and the mixture was extracted with ethyl acetate (10 mL*3). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product which was purified on silica gel column chromatography (from PE/EtOAc=1/0 to 3/1, TLC: PE/EtOAc=2/1, Rf=0.47) to give N-(4-bromophenyl)-2-methyl-pyrazole-3-carboxamide (198 mg, 699.77 mumol, 60.2% yield, 99.0% purity) as a white solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.61 (s, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.47 (s, 4H), 6.63 (d, J=2.0 Hz, 1H), 4.20 (s, 3H); ES-LCMS m/z 279.6 [M+H]+.

According to the analysis of related databases, 16034-46-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyn Therapeutics; Castro, Alfredo C.; Evans, Catherine Anne; (108 pag.)US2019/55218; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 15366-34-4, These common heterocyclic compound, 15366-34-4, name is Methyl 1H-pyrazole-3-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.

A mixture of 3-[5-(bromomethyl)-2-thienyl]-5-(trifluoromethyl)-1 ,2,4-oxadiazole (1.0 g, 3.2 mmol), methyl 1 H-pyrazole-3-carboxylate (600 mg, 4.8 mmol) and potassium carbonate (880 mg, 6.4mmol) in acetonitrile (32 mL) was heated at 1 10C for 2 hours. The orange suspension was filtered to remove the solids and the filtrate solution was then concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography on silica gel using a cyclohexane/ethyl acetate gradient to afford 610 mg of the title compound as a white solid. LC/MS (Method A) retention time = 1.00 minutes, 359 (M+H). 1NMR (400 MHz, CDCI3) delta ppm: 7.78 (d, 1 H), 7.51 (d, 1 H), 7.12 (d, 1 H), 6.89 (d, 1 H), 5.61 (s, 2H), 3.98 (s, 3H). methyl 2-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-3-carboxylate (Compound 1.54 of Table T1 ) was isolated as a byproduct in form of a white solid (274 mg). LC/MS (Method A) retention time = 1.10 minutes, 359 M+H).

The synthetic route of 15366-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; PITTERNA, Thomas; RAJAN, Ramya; (0 pag.)WO2018/158365; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 398495-65-3,Some common heterocyclic compound, 398495-65-3, name is 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, molecular formula is C13H20N4O4, 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 solution of 3-amino-5-tert-butyloxycarbonyl-1-ethoxycarbonyl- -4, 6- dihydropyrrolo [3,4-c] pyrazole (0.4g, 1.35 mmol) in dry tetrahydrofurane [(10ML)] was added drop wise to a solution of isoamylnitrite (0. [32ML,] 2. [36MMOL)] in dry tetrahydrofurane (2ml) maintained at reflux. The resulting solution was stirred at reflux for 4 hours, and then cooled to room temperature. After removal of the solvent under vacuum, the crude material was purified by flash chromatography on silica gel using n- [HEXANE. ETHYL] acetate [90No.10 ]; 70-30. The title compound was obtained as a light yellow oil (200mg, y 53%). [H-NMR] (DMSO-d6) [8] ppm: 7.67 (s, 1H); 4.54 (m, 2H); 4.39 (q, 2H); 4.32 (m, [2H)] ; 1.43 (s, 9H); 1.31 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-tert-Butyl 1-ethyl 3-aminopyrrolo[3,4-c]pyrazole-1,5(4H,6H)-dicarboxylate, its application will become more common.

Reference:
Patent; PHARMACIA ITALIA SPA; WO2004/13144; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, 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. Safety of 1-Methyl-1H-pyrazol-5-amine

3rd Generation BrettPhos precatalyst (22.95 mg, 0.03 mmol) was added to 2-(2-chloro-5- methylpyrimidin-4-yl)-7-((6-(difluoromethyl)pyridin-2-yl)methyl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Intermediate 51; 205 mg, 0.51 mmol), 1-methyl- lH-pyrazol-5-amine (123 mg, 1.27 mmol) and CS2CO3 (330 mg, 1.01 mmol) in 1,4- dioxane (8 mL) at 25°C under nitrogen and the resulting mixture was stirred at 100 °C for 8 hours. The solvent was then removed under reduced pressure. The crude product was purified by flash silica chromatography, elution gradient 0 to 6percent MeOH in DCM. Compound containing fractions were evaporated to dryness to afford a yellow residue. This residue was purified further by preparative HPLC (XSelect CSH Prep C18 OBD column, 5mu silica, 19 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.03percent NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 7-((6-(difluoromethyl)pyridin-2- yl)methyl)-2-(5-methyl-2-((l-methyl-lH-pyrazol-5-yl)amino)pyrimidin-4-yl)-6,7- dihydroimidazo[l,2-a]pyrazin-8(5H)-one (Example 15; 122 mg, 51.8percent) as a white solid. H NMR (400 MHz, DMSO, 20°C) delta 2.50 (3H, s), 3.70 (3H, s), 3.87 – 3.95 (2H, m), 4.42 – 4.50 (2H, m), 4.87 (2H, s), 6.30 (1H, d), 6.95 (1H, t), 7.33 (1H, d), 7.61 (2H, t), 7.94 (1H, s), 8.00 (1H, t), 8.32 (1H, s), 9.24 (1H, s). m/z (ES+), [M+H]+ = 466.

The synthetic route of 1-Methyl-1H-pyrazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; JONES, Clifford, David; SWALLOW, Steven; GRAHAM, Mark, Andrew; DOBSON, Andrew, Hornby; MCCABE, James, Francis; (223 pag.)WO2017/80979; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 42098-25-9, name is 5-Chloro-1-methyl-4-nitro-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. COA of Formula: C4H4ClN3O2

KO’Bu (938 mg, 8.36 mmol) was added to a stirred solution of 5-chloro-l-methyl-4- nitro-lH-pyrazole (900 mg, 5.57 mmol) and cyclopropanol (970.713 mg, 16.713 mmol) in MeCN (7.27 mL) at rt. Addition was done portionwise. The mixture was stirred at rt for 3hours. Water was added and the mixture acidified with 3N HCl(aq). The reaction mixture was extracted with DCM, dried over MgS04, filtered and evaporated. A purification was performed via preparative LC (Stationary phase: irregular SiOH 15- 40muiotaeta 80g GraceResolv, Mobile phase: gradient from 100% DCM to 98% DCM, 2% MeOH, 0, 1% NH4OH) to afford intermediate 620 (470 mg, yield 46 %).

The synthetic route of 5-Chloro-1-methyl-4-nitro-1H-pyrazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics