Tag: M.W:100-200

Application of 5932-27-4,Some common heterocyclic compound, 5932-27-4, name is Ethyl 1H-pyrazole-3-carboxylate, 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.

Description 11: 1-tert-Butoxvcarbonvlmethvl-1 H-pvrazole-4-carboxylic acid ethyl ester Potassium tert butoxide (0.045g) was added, in portions, to a stirred solution of 3- (ethoxycarbonyl) pyrazole [CAS 37622-90-5] (0.050g) in N, N- dimethylformamide (0. 5mol). The mixture was stirred for 5 min then tert- butylbromoacetate (0.078g) was added, in portions over 2 min. The mixture was stirred for 0.75h then partitioned between ethyl acetate (30moi) and 1. 0M aqueous sodium bicarbonate (20ml). The organic phase was separated, washed with water (2x20m1), dried (Na2SO4) and concentrated in vacuo to give the title compound (0.073g) as a colourless, viscous oil. LC-MS: Rt = 2.78min. Mass Spectrum m/z 255 [MH+]

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82862; (2003); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 14531-55-6, The chemical industry reduces the impact on the environment during synthesis 14531-55-6, name is 3,5-Dimethyl-4-nitro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

(a)1-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,5-dimethyl-4-nitro-pyrazoleTo a cold (0 C) solution of 3,5-dimethyl4nitro-1 H-pyrazole (250 mg, 1.77 mmol),triethylene glycol monomethylether (482 IJL, 3.01 mmol) and triphenylphosphine (789 mg, 3.01mmol) in THF (10 mL) was added dropwise a solution of 40% DEAD in toluene (1.31 mL, 3.01 mmol) The reaction mixture was allowed to warm to room temperature and was stirred for 3 h. Ethyl acetate was added and washed with a 10% NaCI-solution. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography(DCM/MeOH = 99/1 to 95/5 v/v%) to afford 1-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3,5- dimethyl-4-nitro-pyrazole (1 .7 g, crude) which was used directly in the next step.

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, 3,5-Dimethyl-4-nitro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; BUIJSMAN, Rogier Christian; STERRENBURG, Jan Gerard; UITDEHAAG, Joost Cornelis Marinus; DE WIT, Joeri Johannes Petrus; ZAMAN, Guido Jenny Rudolf; WO2015/155042; (2015); 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. 25016-12-0, name is 1,3-Dimethyl-1H-pyrazole-4-carbaldehyde belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H8N2O

General procedure: Sodium triacetoxyborohydride (46.3 mg, 0.218 mmol) was added toa mixture of 10c (65 mg, 0.146 mmol) and tetrahydropyran-4-carbaldehyde(18.3 mg, 0.160 mmol) in 1,2-dichloroethane (1.30 mL). The mixture was stirred at room temperature for 2 h, sat.NaHCO3 aqueoussolution was added, and the mixture was extracted with CHCl3. The organic layer was washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CHCl3/MeOH) to give the desired compound as a white solid (41.0 mg, 52%). 1H NMR (DMSO-d6) delta1.00-1.29 (3H, m), 1.44-1.60 (3H, m), 1.64-1.85 (3H, m), 1.95-2.17(5H, m), 2.62-2.71 (1H, m), 2.78-2.88 (1H, m), 3.08 (3H, s), 3.15-3.29(2H, m), 3.70-3.83 (2H, m), 4.01 (3H, s), 4.05 (3H, s), 4.27-4.37 (2H,m), 7.26 (1H, s), 8.11 (1H, s), 8.43 (1H, d, J=2.3 Hz), 8.85 (1H, d,J=2.3 Hz), 9.37 (1H, s); ESI-MS m/z 545.3 [(M+H)+]; HRMS(ESI) m/z calcd for C26H37N6O5S [(M+H)+]: 545.2541, found: 545.2537

The synthetic route of 25016-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hamajima, Toshihiro; Takahashi, Fumie; Kato, Koji; Sugano, Yukihito; Yamaki, Susumu; Moritomo, Ayako; Kubo, Satoshi; Nakamura, Koji; Yamagami, Kaoru; Hamakawa, Nozomu; Yokoo, Koji; Fukahori, Hidehiko; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 3917 – 3924;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 5334-40-7,Some common heterocyclic compound, 5334-40-7, name is 4-Nitro-1H-pyrazole-3-carboxylic acid, molecular formula is C4H3N3O4, 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 4-nitro-1H-pyrazole-3-carboxylic acid (50.0 g, 318 mmol, CAS5334-40-7) in MeOH (250 mL) was added SOCl2 (56.8 g, 477 mmol). The mixture was stirred at 70 C. for 5 hrs. On completion, the mixture was concentrated in vacuo to give the title compound (54.0 g, 99% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta 14.40 (s, 1H), 9.98 (s, 1H), 3.89 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitro-1H-pyrazole-3-carboxylic acid, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 368870-03-5, name is (4-(1H-Pyrazol-1-yl)phenyl)methanamine, 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 368870-03-5, HPLC of Formula: C10H11N3

A solution of ethyl 2-(bromomethyl)-6-methoxybenzoate (0.50 g), (4-(1H-pyrazol-1-yl)phenyl)methanamine (0.32 g) and potassium carbonate (0.38 g) in ethanol (5 mL) was stirred under a nitrogen atmosphere at room temperature overnight. To the reaction solution was added water, and the resulting precipitate was collected by filtration, and dried. To the obtained white solid was added 25% hydrobromic acid (acetic acid solution) (5 mL), and the mixture was stirred under a nitrogen atmosphere at 120C overnight. The reaction solution was neutralized with saturated aqueous sodium hydrogen carbonate solution, and ethyl acetate was added. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by NH silica gel chromatography (hexane-ethyl acetate) to give the title compound (0.31 g). 1H NMR (300 MHz, DMSO-d6) delta 4.31 (2H, s), 4.69 (2H, s), 6.48-6.58 (1H, m), 6.82 (1H, d, J = 8.3 Hz), 6.94 (1H, d, J = 7.6 Hz), 7.30-7.44 (3H, m), 7.73 (1H, d, J = 1.3 Hz), 7.82 (2H, d, J = 8.7 Hz), 8.46 (1H, d, J = 2.3 Hz), 9.63 (1H, brs).

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-(1H-Pyrazol-1-yl)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (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. 25016-11-9, name is 1-Methyl-1H-pyrazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 25016-11-9

To a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (12.60 g, 49.9 mmol) in tetrahydrofuran (THF) (30 mL) was added NaH 60% dispersion in mineral oil (2.179 g, 54.5 mmol) slowly. The mixture was stirred for 10 min at room temperature. A solution of l-methyl-lH-pyrazole-4-carbaldehyde (5.0 g, 45.4 mmol) in tetrahydrofuran (THF) (30 mL) was added slowly. After addition, the reaction mixture was stirred for 20 min at room temperature. The LCMS showed a complete reaction. The mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous MgS04. It was filtered and the filtrate was concentrated to give the crude product which was then purified on the Combiflash column chromatography eluting with a gradient of 0 to 50% ethyl acetate in hexanes. The title compound was obtained as a clear colorless oil (9.0 g, 43.2 mmol, 95 % yield). LC-MS mlz 208.9 (M+H)+, 0.93 min (ret. time).

According to the analysis of related databases, 25016-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BUDZIK, Brian W; LI, Peng; PERO, Joseph E.; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; WILLEMS, Hendrika Maria Gerarda; WOOLFORD, Alison Jo-Anne; (176 pag.)WO2018/109642; (2018); 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. 174891-10-2, name is 5-Amino-1H-pyrazole-3-acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Amino-1H-pyrazole-3-acetic acid

Example 100[0255] To compound 97 (700mg, 4.96mMol) in 7mL of DMF at O0C was added pyridine (883 muL, 863mg, 10.9ImMoI) followed by careful, dropwise addition of pentafluorophenyl trifluoroacetate (1.68mL, 2.78g, 9.92mMol). Reaction mixture was stirred at 0 C for 10 minutes and 90 minutes at room temperature. 2-chloro-6-methylaniline (1.22mL, 1.4g, 9.92mMol) was added and reaction mixture was stirred overnight at room temperature. Reaction was poured into 5OmL of IN HCl, organic layer was separated. Aqueous layer was extracted with EtOAc. Organic fractions were combined, washed with brine, dried over Na2SO4, filtered and solvent was evaporated to give 1.79g (quant.) of crude product 100 that was used in the next step without purification.

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 174891-10-2.

Reference:
Patent; ABRAXIS BIOSCIENCE, LLC; TAO, Chunlin; WANG, Qinwei; NALLAN, Laxman; POLAT, Tulay; KORONIAK, Lukasz; DESAI, Neil; WO2010/144338; (2010); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1621-91-6,Some common heterocyclic compound, 1621-91-6, name is 1H-Pyrazole-3-carboxylic acid, molecular formula is C4H4N2O2, 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.

Step 1 : To a mixture of 1 H-pyrazole-3-carboxylic acid (15.0 g, 134 mmol) and Cs2C03 (109 g, 335 mmol) in CH3CN (250 mL) was added CH3I (29.2 ml, 469 mmol) and the RM was stirred at rt for 14 h. The RM was filtered and filtrate was concentrated under reduced pressure, diluted with EtOAc and washed with water and brine before being dried. The solvent was evaporated under reduced pressure to give the crude product which was purified by CC (Si02; EtOAc/Hex) to yield the desired product (10.0 g, 53%). LC-MS (Method 3): m/z [M+H]+ = 141.3 (MW calc. 140.14); R, = 1.55 min.

The synthetic route of 1621-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, Felix; RITTER, Stefanie; NORDHOFF, Sonja; WACHTEN, Sebastian; OBERBOeRSCH, Stefan; KLESS, Achim; WO2015/22073; (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. 1203705-55-8, name is 3-Bromo-1H-pyrazol-5-amine, A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-1H-pyrazol-5-amine

A mixture of methyl 2-hydroxy-4-oxo-4-(pyridin-2-yl)but-2-enoate [1224740-13-9] (730 mg, 3.52 mmol) and 3-bromo-lH-pyrazol-5-amine [950739-21-6] (628 mg, 3.88 mmol) in MeOH (17 mL) was stirred under reflux for 18 h. The reaction mixture was cooled to rt and the precipitate was filtered off, rinsed with MeOH and dried. The residue (546 mg) was purified via achiral SFC (Stationary phase: Lux Cellulose-2 5 pm 250*30mm, mobile phase: 60% C02, 40% MeOH) to afford intermediate 1171 (147 mg, 13%) as a yellow solid.

The synthetic route of 1203705-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; LANCOIS, David Francis Alain; GUILLEMONT, Jerome Emile Georges; RABOISSON, Pierre Jean-Marie Bernard; ROYMANS, Dirk Andre Emmy; RIGAUX, Peter; MICHAUT, Antoine Benjamin; MERCEY, Guillaume Jean Maurice; (295 pag.)WO2019/106004; (2019); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 16617-46-2,Some common heterocyclic compound, 16617-46-2, name is 3-Amino-1H-pyrazole-4-carbonitrile, molecular formula is C4H4N4, 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 compound II (2.6 g, 10 mmol) and nitrile III (1.1 g, 10.2 mmol) in ethanol (30 ml) was dissolved at lab temperature and then, a saturated solution of hydrogen chloride in ethanol (1 ml) was added. The resulting mixture was boiled for 2 hours using a reflux condenser and, then, cooled down to 5 to 10 °C and the precipitated crystals were sucked off, washed with water and air dried. 2.6 g of crude product (85percent), m. p. 184-188 °C were obtained. After crystallization, 2.4 g (79percent) of crystals were obtained with m. p. 187-188 °C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-1H-pyrazole-4-carbonitrile, its application will become more common.

Reference:
Patent; ZENTIVA, A.S.; WO2004/37824; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics