Category: pyrazoles-derivatives

Synthetic Route of 694-48-4,Some common heterocyclic compound, 694-48-4, name is 1,3-Dimethyl-1H-pyrazole, molecular formula is C5H8N2, 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.

In a three-necked reaction flask equipped with a stirrer, 50 ml of acetic anhydride and 12.7 g of nitric acid were added,1,3-dimethylpyrazole 9.7 g of acetic anhydride in 10 ml was slowly added dropwise to the mixed acid,Add 50-60 degrees after the end of the reaction until the reaction is complete,Cooled to room temperature to add 100 grams of ice water,Filtered and dried to give 12 g of 4-nitro-1,3-dimethylpyrazole,LC purity 80%, yield: 84%.

The synthetic route of 694-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Hande Chuanghong Biochemical Technology Co., Ltd.; Mao Zhongping; Ma Dongxu; Ge Yonghui; Ren Xuejing; Tan Jin; (9 pag.)CN106674116; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 478968-48-8, name is Ethyl 3-methoxy-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 478968-48-8, name: Ethyl 3-methoxy-1H-pyrazole-4-carboxylate

A mixture of ethyl 3-methoxy- 1H-pyrazole-4-carboxylate (1.116 g, 6.56 mmol, 1.00 equiv) in N,N-dimethylformamide (60 mL), L-Proline (151 mg, 1.31 mmol, 0.20 equiv), CuT (128 mg, 0.67 mmol, 0.10 equiv), 2-chloro-5 -(trifluoromethyl)pyrazine (1.19 g, 6.52 mmol, 1.00 equiv), and potassium carbonate (2.72 g, 19.68 mmol, 3.00 equiv) was stuffed overnight at 100C under nitrogen. The solids were filtered out. The filtrate was diluted with 500 mL of ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (5:100) to afford the title compound (1 g, 48%) as an off-white solid.

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Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2075-46-9, name is 4-Nitro-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 2075-46-9, Application In Synthesis of 4-Nitro-1H-pyrazole

4-Nitro-1H-pyrazole (1.13 g, 9.99 mmol) was dissolved in 15 mL of dry THF.The reaction flask was placed in an ice bath and cooled, and NaH (600 mg, 25 mmol) was slowly added.Stir to room temperature and stir for 2.5 h, then slowly add methyl iodide (3.84 g, 20 mmol).Stirring was continued for 1.5 h, and the reaction was quenched by slowly adding 15 mL of saturated brine.The reaction solution was concentrated under reduced pressure and ethyl acetate (50 mL×3)Wash with water, saturated brine (50 mL×2), dry over anhydrous sodium sulfate,1-Methyl-4-nitro-1H-pyrazole (826 mg, 65%) was obtained as a pale yellow solid.

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, 4-Nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Diao Pharmaceutical Group Co., Ltd.; Guo Na; He Qian; Deng Ta; Dai Chuan; Yang Qiao; Chen Shuang; Fan Bo; (131 pag.)CN108373476; (2018); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 1192-21-8, 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.

To a mixture of (i?)-2-(2-chloro-5-methylpyrimidin-4-yl)-7-(3,4-difluorobenzyl)-6- (methoxymethyl)-6,7-dihydroimidazo[l ,2-a]pyrazin-8(5H)-one (Intermediate 62; 104.7 g, 225.64 mmol), 1 -methyl- lH-pyrazol-5-amine (33.5 g, 338.47 mmol) in 2-methyl tetrahydrofuran (1200 mL) and CS2CO3 (147 g, 451.29 mmol) in water (120 mL) were added 2′-(dicyclohexylphosphanyl)-N,N-dimethyl-[l, -biphenyl]-2-amine (7.10 g, 18.05 mmol) and Pd2(dba)3 (8.27 g, 9.03 mmol) at 25 °C under nitrogen. The resulting mixture was degassed 3 times under nitrogen and then stirred at 70 °C for 24 hours. The reaction mixture was cooled to room temperature and the layers were separated. The organic layer was washed successively with water (500 mL), aqueous citric acid (IN, 600 mL) and water (200 mL). Silicycle (Si-SH, 150 g) was added to the organic layer at 40 °C and stirred for 20 hours. After filtration the filtrate was concentrated and the residue was purified by SFC chromatography using a Kromasil DIOL column, elution gradient 25percent EtOH/NH3 100/0.5 in C02, 140 bar. Pure fractions were evaporated to dryness to afford (i?)-7-(3,4- difluorobenzyl)-6-(methoxymethyl)-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 18; 72.6 g, 65percent) as a solid. NMR (500 MHz, DMSO) delta 2.51 (3H, s), 3.17 (3H, s), 3.30 (1H, dd), 3.39 (1H, dd), 3.69 (3H, s), 4.03 (1H, dtd), 4.38 (1H, d), 4.44 (1H, dd), 4.51 (1H, dd), 5.08 (1H, d), 6.30 (1H, d), 7.22 – 7.28 (1H, m), 7.33 (1H, d), 7.41 (1H, dt), 7.47 (1H, ddd), 7.93 (1H, s), 8.31 (1H, s), 9.21 (1H, s). m/z (ES+), [M+H]+ = 495

The synthetic route of 1192-21-8 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

52222-73-8, name is 4-(Trifluoromethyl)-1H-pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 4-(Trifluoromethyl)-1H-pyrazole

To a solution of 7′-(2,6-difluoro-4-iodo-phenyl)spiro[cyclopropane-l,5′-imidazo[l,2- a]imidazole]-6′-one (Example A.3) (300 mg, 0.770 mmol, 1 eq.) and 4-(trifluoromethyl)-lH- pyrazole (158 mg, 1.16 mmol, 1.5 eq.) in toluene (1.5 mL) was added K3P04 (494 mg, 2.32 mmol, 3 eq.) and 1,2-N,N’ dimethyl- 1 ,2-cyclohexanediamine (23 mg, 0.160 mmol, 0.21 eq.) and degassed with nitrogen for 10 min. Cul (15 mg, 0.080 mmol, 0.1 eq.) was added, the reaction mixture again degassed with nitrogen for 10 mins, and stirred at 130 C in the microwave for 1 h. The reaction mixture was diluted with EtOAc (50 ml), the organics washed with water (2 x 20 mL) and brine (20 mL), dried over Na2S04, concentrated in vacuo and purified by flash chromatography over silica gel (50 % EtOAc in hexane) to yield 7′-[2,6-difluoro-4-[4- (trifluoromethyl)pyrazol-l-yl]phenyl]spiro[cyclopropane-l,5′-imidazo[l,2-a]imidazole]-6′-one (40 mg, 0.1 mmol, 13 % yield) as a sticky gel. M+H+ = 396.0.

The synthetic route of 52222-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; JAESCHKE, Georg; O`HARA, Fionn; VIEIRA, Eric; (85 pag.)WO2019/34713; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 1260243-04-6,Some common heterocyclic compound, 1260243-04-6, name is Ethyl 5-amino-1H-pyrazole-4-carboxylate, molecular formula is C6H9N3O2, 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.

Ethyl 5-amino-1H-pyrazole-4-carboxylate (15.5 g, 0.1 mol) obtained in step 1) And 1-p-fluorophenyl-4,4,4-trifluorobutanedione (23.4 g, 0.1 mol) obtained in step 2) were placed in a vessel; The mixture in the container was dissolved using 50 mL of glacial acetic acid to give a mixture E, the vessel was placed under an electrothermal condition and heated to 115 ° C; The mixture E was heated to reflux, and after 7 hours, the mixture was allowed to stand for cooling to remove the yellow-green needle-like solid; the solid was filtered, washed and dried, To give ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate; and the article used for the washing process is cold glacial acetic acid. The resulting product The mass of ethyl 5- (4-fluorophenyl) -7-trifluoromethylpyrazolo [1,5-a] pyrimidine-3-carboxylate was 27.05 g. Yield: 76.63percent.

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

Reference:
Patent; Chongqing MedicalCollege; NIU, YAHUI; SHI, LEI; (10 pag.)CN105949202; (2016); A;,
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. 3528-45-8, name is 1-(4-Methoxybenzyl)-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Product Details of 3528-45-8

To an ice-cooled solution of 2-(4-methoxy-benzyl)-2eta-pyrazol-3-ylamine (406 mg, 2.0 mmol, 1.0 eq.) in DCM (5 mL), DIPEA (0.52 ml, 3.0 mmol, 1.5 eq.) was added.A solution of bromoacetyl bromide (0.19 ml, 2.2 mmol, 1.1 eq.) in DCM (2 mL) was added dropwise. The cooling bath was removed and the brown solution was stirred at r.t. for 1.5 hours. The solution was diluted with AcOEt (75 mL), washed with sat. aq.NaHCO3 soln. (1 x 40 mL), with sat. aq. NaCl soln. (1 x 40 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by CC (SiO2, AcOEt/Hept 1 :1 to6:4) to give the desired bromide as a beige solid.LC-MS (A): tR = 2.60 min; [M-H]+ = 322.3.

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; ACTELION PHARMACEUTICALS LTD; WO2009/150614; (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. 132712-71-1, name is 3-Methyl-1H-pyrazol-5-ol belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 3-Methyl-1H-pyrazol-5-ol

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95%, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol %) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

The synthetic route of 132712-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 37622-90-5, A common heterocyclic compound, 37622-90-5, name is Ethyl 4-pyrazolecarboxylate, molecular formula is C6H8N2O2, 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.

Preparation 8; Preparation of HI-ftert-butoxycarbonylt°iperidin-^yll-IH-pyrazole-Phicarboxylic acid; A mixture of ethyl 1H-pyrazole-4-carboxylate (700 mg, 5 mmol) and NaH 60% (6 mmol) was stirred under nitrogen at 00C for 1 hour in dry DMF (15 mL). ferf-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (1.53 gr, 5.5 mmol) dissolved in 4 mL of dry DMF was added and the resulting solution was hetaed at 100C overnight . Reaction mixture was quenched with water and extracted (x3) with ethyl acetate. Collected organic phases were dried over Na2SU4, filtered and evaporated to dryness. Residue was dissolved in MeOH (20 mL) and water (5 mL) and KOH (1.12 gr, 20 mmol) was added. The resulting solution was stirred at room temperature 24 hours, then solvents removed under reduced pressure. The residue was taken-up with AcOEt and KHSO4 5% solution. Acqueous phase was extracted with EtOAc several times. Collected organic phases were dried with Na2SU4, filtered and evaporated to dryness affording 600 mg of the title compound. 1 H-NMR (400 MHz), delta (ppm, DMSO-de): 1.42 (s, 9H) 1.73 – 1.87 (m, 2H) 1.96 – 2.03 (m, 2H) 2.82 – 2.99 (m, 2H) 4.04 (d, J=12.93 Hz, 2H) 4.34 – 4.47 (m, 1H) 7.81 (s, 1H) 8.29 (s, 1H) 12.26 (br. s., 1H)

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; NERVIANO MEDICAL SCIENCES S.r.l.; MENICHINCHERI, Maria; BERTRAND, Jay, Aaron; MARCHIONNI, Chiara; NESI, Marcella; ORSINI, Paolo; PANZERI, Achille; WO2010/69966; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 26308-42-9,Some common heterocyclic compound, 26308-42-9, name is 3-Ethyl-1-methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C7H10N2O2, 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 50 mL round bottom flask equipped with a magnetic stirrer was added 1-methyl-3-ethyl-1-hydrogen-pyrazole-5-carboxylic acid(154 mg, 1.0 mmol, 1.0 eq),Selectfluor (708 mg, 2.0 mmol, 2.0 eq), lithium acetate (264 mg, 4.0 mmol,4.0 eq); then dichloroethane (3.3 mL) and water (1.7 mL) were added as solvent; the reaction vessel was sealed at 50 C in an oil bathAnd the mixture was heated and stirred for 15 hours. After the reaction was completed, the reaction mixture was extracted twice with 20 mL of ether, and the organic phaseAnd washed with saturated brine, and then dried over anhydrous sodium sulfate. After drying, the organic solvent was dried under reduced pressure to obtain crude productThe crude product was subjected to column separation using analytically pure n-pentane as eluent to give the final product: 1,1′-diethyl-5,5′-difluoro-3,3′-dimethyl-1-hydrogen, 1′-hydro-4,4′-bipyrazole as a colorless oil in 82% yield.

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

Reference:
Patent; Central South University; Tang, Zhenyu; Yuan, Xi; Yao, Jianfei; (24 pag.)CN106397377; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics