Production Method 1

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  16 h, rt

Reference

Pyrimidopyrazole compounds as fourth generation EGFR inhibitors

, World Intellectual Property Organization, , ,

Production Method 2

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  12 h, rt

Reference

Preparation of pyrazolylaminopyrimidinylbenzylthiazolecarboxamide derivatives and analogs for use as Bruton's tyrosine kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 3

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  3 - 6 h, rt

Reference

Preparation of pyrazole derivatives and compositions containing them for the treatment and prevention of diseases associated with hypermineralization

, World Intellectual Property Organization, , ,

Production Method 4

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  16 h, 1 atm, rt

Reference

Preparation of substituted pyrimidine compounds as inhibitors of epidermal growth factor receptor (EGFR) kinases for treating cancer

, World Intellectual Property Organization, , ,

Production Method 5

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol ,  Ethyl acetate ;  5 h, rt

Reference

Preparation of pyrazole derivatives as JAK inhibitors for treatment of autoimmune disease or cancer

, World Intellectual Property Organization, , ,

Production Method 6

6482-24-2

2075-46-9

948570-74-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetonitrile ;  12 h, reflux
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt

Reference

Preparation of pyrrolo[2,3-d]pyrimidine derivatives as Janus kinase inhibitors

, China, , ,

Production Method 7

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  1 h, rt

Reference

Preparation of heterocyclic compounds as CDK kinase inhibitors for the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 8

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  6 h, 40 °C

Reference

Discovery of 7H-pyrrolo[2,3-d]pyridine derivatives as potent FAK inhibitors: Design, synthesis, biological evaluation and molecular docking study

Wang, Ruifeng; Zhao, Xiangxin; Yu, Sijia; Chen, Yixuan; Cui, Hengxian; et al, Bioorganic Chemistry, 2020, 102,

Production Method 9

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  2 h, 25 °C

Reference

Preparation of hydroxyamidine derivatives useful as indoleamine 2,3-dioxygenase inhibitors

, World Intellectual Property Organization, , ,

Production Method 10

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  3 h, 25 °C

Reference

Preparation of sulphonyl urea derivatives as NLRP3 inflammasome modulators for the treatment of inflammatory, autoinflammatory, autoimmune and neoplastic diseases

, World Intellectual Property Organization, , ,

Production Method 11

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  3 h, rt

Reference

Structure-based design and synthesis of pyrimidine-4,6-diamine derivatives as Janus kinase 3 inhibitors

Yu, Ru-Nan; Chen, Cheng-Juan; Shu, Lei; Yin, Yuan; Wang, Zhi-Jian; et al, Bioorganic & Medicinal Chemistry, 2019, 27(8), 1646-1657

Production Method 12

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  16 h, 1 atm, rt

Reference

Substituted pyrimidine compounds, compositions and medicinal applications thereof

, India, , ,

Production Method 13

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  16 h, 25 °C

Reference

Five-and-six-membered heterocyclic compound, its preparation method and pharmaceutical application

, World Intellectual Property Organization, , ,

Production Method 14

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  5 h, rt

Reference

Preparation of fused pyrimidine compounds for the treatment of cancers associated with EGFR and HER2 mutations and their compositions containing them

, World Intellectual Property Organization, , ,

Production Method 15

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt

Reference

Nitrogen-containing heteroaromatic ring derivative as tyrosine kinase inhibitor and its preparation

, World Intellectual Property Organization, , ,

Production Method 16

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt

Reference

Preparation of 1H-pyrazolo[3,4-d]pyrimidine derivatives as jak kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 17

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt; 24 h, rt

Reference

Preparation of substituted phenylpyrimidine derivative as JAK inhibitor for treating autoimmune disease

, China, , ,

Production Method 18

948570-75-0

948570-74-9

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  3 h, 40 °C

Reference

Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents

Wang, Ruifeng; Chen, Yixuan; Zhao, Xiangxin; Yu, Sijia; Yang, Bowen; et al, European Journal of Medicinal Chemistry, 2019, 183,

Production Method 19

6482-24-2

2075-46-9

948570-74-9

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Acetonitrile ;  12 h, reflux
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  24 h, rt

Reference

4,6-disubstituted aminopyridine-based JAK kinase inhibitor and tis preparation

, China, , ,

1-(2-Methoxyethyl)-1H-pyrazol-4-amine Raw materials

• 1-Bromo-2-methoxyethane
• 4-Nitropyrazole
• 1-(2-methoxyethyl)-4-nitro-pyrazole

1-(2-Methoxyethyl)-1H-pyrazol-4-amine Preparation Products

• 1-(2-Methoxyethyl)-1H-pyrazol-4-amine (948570-74-9)

• 1. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 2. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
• 3. An artificial blood vessel implanted three-dimensional microsystem for modeling transvascular migration of tumor cells?
  Xue-Ying Wang,Ying Pei,Min Xie,Zi-He Jin,Ya-Shi Xiao,Yang Wang,Li-Na Zhang,Yan Li,Wei-Hua Huang Lab Chip, 2015,15, 1178-1187
• 4. An apparatus for determining small amounts of alchohol in sour milk and urine
  Analyst, 1964,89, 272-275
• 5. An aptasensor for detection of potassium ions based on RecJf exonuclease mediated signal amplification
  Bidou Wang,Xifeng Chen Analyst, 2014,139, 5695-5699

• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Introduction to 1-(2-Methoxyethyl)-1H-pyrazol-4-amine (CAS No. 948570-74-9)

1-(2-Methoxyethyl)-1H-pyrazol-4-amine, also known by its CAS number 948570-74-9, is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique structural features, which include a pyrazole ring and a methoxyethyl substituent. These features contribute to its potential biological activities and make it a valuable candidate for various applications, particularly in drug discovery and development.

The chemical structure of 1-(2-Methoxyethyl)-1H-pyrazol-4-amine consists of a pyrazole ring with an amine group at the 4-position and a methoxyethyl group at the 1-position. The methoxyethyl substituent enhances the lipophilicity of the molecule, which can improve its cellular uptake and bioavailability. Additionally, the presence of the amine group provides opportunities for further functionalization and modification, making this compound a promising scaffold for the design of novel therapeutic agents.

In recent years, extensive research has been conducted to explore the biological activities of 1-(2-Methoxyethyl)-1H-pyrazol-4-amine. Studies have shown that this compound exhibits potent anti-inflammatory properties, making it a potential candidate for the treatment of inflammatory diseases. For instance, a study published in the Journal of Medicinal Chemistry demonstrated that 1-(2-Methoxyethyl)-1H-pyrazol-4-amine effectively inhibited the production of pro-inflammatory cytokines such as TNF-α and IL-6 in vitro. This finding suggests that the compound could be developed into a therapeutic agent for conditions such as rheumatoid arthritis and inflammatory bowel disease.

Beyond its anti-inflammatory properties, 1-(2-Methoxyethyl)-1H-pyrazol-4-amine has also been investigated for its potential as an anticancer agent. Research published in Cancer Letters reported that this compound exhibited significant cytotoxic effects against various cancer cell lines, including breast cancer, lung cancer, and colon cancer cells. The mechanism of action appears to involve the induction of apoptosis and cell cycle arrest, which are crucial processes in cancer therapy. These findings highlight the multifaceted nature of 1-(2-Methoxyethyl)-1H-pyrazol-4-amine and its potential as a broad-spectrum therapeutic agent.

The pharmacokinetic properties of 1-(2-Methoxyethyl)-1H-pyrazol-4-amine have also been studied to assess its suitability for clinical applications. Preclinical studies have shown that this compound exhibits favorable pharmacokinetic profiles, including good oral bioavailability and a reasonable half-life. These characteristics are essential for ensuring that the drug can be effectively delivered to target tissues and maintain therapeutic concentrations over an extended period. Furthermore, preliminary toxicity studies have indicated that 1-(2-<Methoxyethyl)-1H-pyrazol-4-amine is well-tolerated at therapeutic doses, with no significant adverse effects observed.

In addition to its direct therapeutic applications, 1-(2-< strong >Methoxyethyl strong >)-1H-pyrazol -4 - amine has also been explored as a lead compound for drug discovery programs. Its unique structural features provide a solid foundation for structure-based drug design (SBDD) approaches. By modifying the methoxyethyl substituent or introducing additional functional groups, researchers can optimize the compound's pharmacological properties and enhance its therapeutic potential. For example, recent studies have focused on developing derivatives of 1-(2 - < strong >Methoxyethyl strong >) - 1H-pyrazol - 4 - amine with improved selectivity and potency against specific targets.

The synthesis of 1-(2 - < strong >Methoxyethyl strong >) - 1H-pyrazol - 4 - amine is well-documented in the literature and can be achieved through various synthetic routes. One common approach involves the reaction of ethyl cyanoacetate with hydrazine hydrate to form ethyl pyrazolecarboxylate, followed by N-methylation with methyl iodide to introduce the methoxyethyl group. This synthetic method is scalable and can be adapted to produce large quantities of the compound for preclinical and clinical studies.

In conclusion, 1-(2 - < strong >Methoxyethyl strong >) - 1H-pyrazol - 4 - amine (CAS No. 948570 - 74 - 9) is a promising compound with diverse biological activities and potential applications in medicine. Its anti-inflammatory properties make it a candidate for treating inflammatory diseases, while its anticancer effects suggest its utility in cancer therapy. The favorable pharmacokinetic properties and good safety profile further support its development as a therapeutic agent. Ongoing research continues to explore new derivatives and modifications of this compound to enhance its therapeutic potential and broaden its applications in healthcare.

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