Tag: M.W:100-200

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. 105434-90-0, name is Ethyl 5-amino-1H-pyrazole-3-carboxylate belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 5-amino-1H-pyrazole-3-carboxylate

Subsequently, to a solution of ethyl 5-amino-3-pyrazolecarboxylate (1.337 g) in tetrahydrofuran (15 mL) was added pyridine (1.385 mL), and then a solution of 4,5-difluoro-2-methyl-benzoyl chloride in tetrahydrofuran (2 mL) was added dropwise with ice cooling. After stirring overnight at room temperature, ethanol (5 mL) and water (45 mL) were added to the reaction mixture, and the precipitated solid was collected by filtration to obtain the title compound (2.271 g) as a white solid.

The synthetic route of 105434-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JAPAN TOBACCO, INC.; US2009/36450; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2075-45-8, name is 4-Bromo-1H-pyrazole, molecular formula is C3H3BrN2, 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: C3H3BrN2

A 500 mL Schlenk flask backfilled with N2was added 4-bromo-1H-pyrazole (10.0g, 68.0 mmol) and dry THF (250 mL). The resulting solution was cooled to 0 C understirring before 60% NaH dispersion (3.3 g, 81.6 mmol) was added slowly. Once H2evolution had ceased, trityl chloride (20.9 g, 74.8 mmol) was added slowly, andthe resulting mixture was stirred overnight at RT before quenching with H2O(5 mL) and drying in vacuo.Theresulting residue was triturated in dichloromethane (5 mL) and methanol (200mL) for 2 hours.The resulting suspension wasfiltered and dried overnight at 50C to give4-bromo-1-trityl-1H-pyrazole(26.0g, 66.8 mmol, 98.2%) as a white solid.1HNMR (300 MHz, DMSO-d6)delta = 7.03 – 7.06 (m, 6 H), 7.34 – 7.40 (m, 9 H), 7.51 (s, 1 H), delta 7.76 (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 2075-45-8, its application will become more common.

Reference:
Article; Kershaw Cook, Laurence J.; Kearsey, Rachel; Lamb, Jessica V.; Pace, Edward J.; Gould, Jamie A.; Tetrahedron Letters; vol. 57; 8; (2016); p. 895 – 898;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 25016-09-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 25016-09-5 name is 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

1 Preparation of 2-pyridyl-(1,3-dimethyl-5-pyrazolyl)methanol: 300 ml of dry tetrahydrofuran solution containing 5.5 g of 2-bromopyridine was cooled to -78C, and 5.45 g of n-butyl lithium hexane solution (15 w/w %) was dropwise added thereto and stirred for 30 minutes. Then, 4.2 g of 1,3-dimethyl-5-formylpyrazole was dropwise added thereto. Afterwards, this was gradually heated up to room temperature and stirred for 15 hours. The solution was neutralized by adding 2 N hydrochloric acid thereto, and then extracted three times each with 150 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel column chromatography (developing solution; chloroform) to give 5.2 g of 2-pyridyl-(1,3-dimethyl-5-pyrazolyl)methanol as a brown oily product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dimethyl-1H-pyrazole-5-carbaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LIMITED; EP556396; (1993); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 143426-52-2, The chemical industry reduces the impact on the environment during synthesis 143426-52-2, name is 1-(4-(Chloromethyl)phenyl)-1H-pyrazole, I believe this compound will play a more active role in future production and life.

3 mmol of the compound IIIe was dissolved in 25 mL of DMSO, followed by the addition of 8 mmol of sodium carbonate. To the solution was added thereto at room temperature, the solution was heated to 85 C for 20 hours.The reaction was quenched, the reaction was poured intoa beakercontaining 100 mL of water, extracted several times with ethyl acetate, dried over anhydrous sodium sulfate, and the mother liquor was evaporated to dryness under reduced pressure. The resulting residue was purified bycolumn chromatography to give the title compound Ie

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-(4-(Chloromethyl)phenyl)-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nantong University; Dai Hong; Shi Yujun; Yao Wei; Song Chan; Qian Hongwei; Wang Xianglong; Zhang Zhou; Han Xudong; (16 pag.)CN106946782; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14531-55-6,Some common heterocyclic compound, 14531-55-6, name is 3,5-Dimethyl-4-nitro-1H-pyrazole, molecular formula is C5H7N3O2, 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-4-nitropyrazole (Fluorochem, Derbyshire, UK1 989 mg, 7 01 mmol) in DMF (40 ml) was added in two portions 55% NaH in oil (420 mg, 9 63 mmol) The reaction mixture was stirred for 30 mm at rt then 2-bromoethyl methyl ether (Aldrich, Buchs, Switzerland, 1 17 g, 8 42 mmol) was added and the reaction mixture stirred for 2 h at rt The reaction mixture was quenched wtth water and extracted with EtOAc The organic layer was washed with water (2x) and brine (2x), d?ed over Na2SO4, filtered and evaporated The crude product was purified by Prep HPLC (H2O (0 1% TFA)/CH3CN 95 5 to 50 50 ?verse phase silica gel) The fractions containing product were collected together, basified with NaHCO3 and concentrated before being extracted with EtOAc (3x) The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a white solid (HPLC tR 2 57 mm (Method A), M+H = 200 MS-ES).

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-Dimethyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; KALTHOFF, Frank Stephan; MAH, Robert; RAGOT, Christian; STAUFFER, Frederic; WO2010/139731; (2010); 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. 151521-49-2, name is 4-Isopropyl-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Isopropyl-1H-pyrazol-5-amine

To a mixture of compound G3 (5.00 g, 40.0 mmol) in anhydrous DCM (25 mL) was added a mixture of ethoxycarbonyl isothiocyanate (4.72 g, 36.0 mmol) in anhydrous DCM (25 mL) at -70C and stirred at -70C for 1 hour, a lot of white solid appeared. TLC showed the reaction was completed. Then the mixture was allowed to warm to -l0C and filtered, and the filter cake was washed with DCM (15 mL) to give 4.50 g of desired compound as a white solid, the structure was confirmed by HNMR. The filtrate was purified by silica gel column to give compound G4 (1.80 g) as a white solid.

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; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; KOCH, Uwe; (138 pag.)WO2019/197546; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 16034-46-1,Some common heterocyclic compound, 16034-46-1, name is 1-Methyl-1H-pyrazole-5-carboxylic acid, molecular formula is C5H6N2O2, 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.

DIPEA (1.05 mL, 6.35 mmol) was added to a stirred solution of Intermediate 1130 (500 mg, 2.12 mmol), 1-methyl-1H-pyrazole-5-carboxylic acid (269 mg, 2.12 mmol) andHATU (969 mg, 2.55 mmol) in anhydrous DMF (10 mL) under a nitrogen atmosphere.The mixture was stirred at 20C for 18 h, then quenched with saturated aqueous sodiumhydrogen carbonate solution (50 mL) and water (50 mL). The material was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (2 x50 mL) and dried over sodium sulfate, then filtered and concentrated in vacuo. Theresidue was purified by flash column chromatography, using a gradient of ethyl acetate inheptane (0-100%), to afford the title compound (618 mg, 99%) as a yellow-orange oil. DH5 (500 MHz, DMSO-d6) 8.60 (d,J8.3 Hz, 1H), 7.46 (d,J2.1 Hz, 1H), 7.01 (d,J2.1 Hz,1H), 4.37 (t, J8.1 Hz, 1H), 4.01 (s, 3H), 3.66 (s, 3H), 2.22-2.08 (m, 1H), 1.80-1.38 (m,13H), 1.37-1.29 (m, 1H). HPLC-MS (method 5): MH+ m/z 308, RT 1.87 minutes.

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-1H-pyrazole-5-carboxylic acid, its application will become more common.

Reference:
Patent; UCB BIOPHARMA SPRL; BRACE, Gareth Neil; CHAPPELL, Rose Elizabeth; DEBOVES, Herve Jean Claude; FOLEY, Anne Marie; FOULKES, Gregory; JONES, Elizabeth Pearl; LECOMTE, Fabien Claude; QUINCEY, Joanna Rachel; SCHULZE, Monika-Sarah Elisabeth Dorothea; SELBY, Matthew Duncan; SMALLEY, Adam Peter; TAYLOR, Richard David; TOWNSEND, Robert James; ZHU, Zhaoning; (278 pag.)WO2018/229079; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 64517-88-0, 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. 64517-88-0, name is 1,3-Dimethyl-1H-pyrazol-4-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 48 2-({5-Chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)-amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide A microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (250 mg, 0.8 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (187 mg, 1.68 mmol), cesium carbonate (783 mg, 2.4 mmol) and dioxane/THF (3:1 ml). The reaction mixture was degassed under nitrogen for 10 min and palladium (II) acetate (9 mg, 0.04 mmol) and BINAP (50 mg, 0.08 mmol) were added. The mixture was stirred in a microwave at 140 C. for 40 min. It was evaporated and the residue dissolved in MeOH was filtered thru celite and thru an Acrodisc and purified further using preparative Agilent HPLC (5 to 95% water:acetonitrile with 0.1% formic acid). Fractions were combined and evaporated. Ether was added to the residue and a tan precipitate crashed out. It was filtered off and dried under vacuum at 40 C. for 2 days to afford the desired product (55 mg, 18%) as a tan solid. LC-MS (ES) m/z=387.1, [M+H]+=389.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 11.93 (br. s., 1H) 9.51 (br. s., 1H) 8.03 (s, 1H) 7.96 (s, 1H) 7.82 (s, 1H) 7.51-7.61 (m, 3H) 7.07-7.15 (m, 1H) 6.68 (s, 1H) 3.70 (d, J=4.29 Hz, 6H) 2.07 (s, 3H).

The synthetic route of 1,3-Dimethyl-1H-pyrazol-4-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ADAMS, Jerry Leroy; Faitg, Thomas H.; Johnson, Neil W.; Lin, Hong; US2010/113475; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 133228-21-4, name is N,N-Dimethyl-1H-pyrazole-1-sulfonamide, 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 133228-21-4, category: pyrazoles-derivatives

12. 3-Ethyl-pyrazole-l-sulphonic acid dimethylamideTo a solution of pyrazole-1-sulphonic acid dimethylamide (13. Ig, 74.9 mmol) in anhydrous tetrahydrofuran (100 ml) at -78 0C under a nitrogen atmosphere was added dropwise a solution of n-butyl lithium in hexanes (1.6M, 51 ml, 82.3 mmol). The reaction was stirred thus for 30 minutes then iodoethane (6.6 ml, 82.4 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature then stirred thus over the weekend. EPO Water was then added and the solution was extracted with ethyl acetate. The separated organic liquors were washed with brine, dried (MgSO4) and concentrated to furnish the title compound as a yellow/ brown oil (12.6g, 85%).

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, N,N-Dimethyl-1H-pyrazole-1-sulfonamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; ASTRAZENECA AB; WO2006/136829; (2006); A2;,
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. 1128-54-7, name is 3-Methyl-1-phenyl-1H-pyrazole, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H10N2

General procedure: A clean and oven dry sealed tube was charged with 1-phenylpyrazole (1equiv.), and styrene (2.5equiv.), to this added (Rh-Complex 0.5mol%) and Cu(OAc)2.H2O (1 equiv), of water (1mL) as a reaction medium. Thereafter, the reaction mixture was heated at 90-100C under sealed conditions for 12h. The gain in product formation was examined by periodic monitoring through TLC. Then the reaction mixture was cool to room temperature, added water (50mL) and EtOAc (75mL) and the organic layer was extracted thrice, and dried over the anhydrous Na2SO4. The crude product was obtained by evaporating the solvent under reduced pressure. Finally, the product was purified through column chromatography (EtOAc/hexane).

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 1128-54-7.

Reference:
Article; Satrawala, Naveen; Williams, Cody; Srivastava, Avinash K.; Sharma, Kamal N.; Smith, Gregory S.; Joshi, Raj K.; Catalysis Communications; vol. 129; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics