1223404-88-3

Basic information

• Product Name: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine
• Synonyms: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine
• CAS NO: 1223404-88-3
• Molecular Formula: C₁₆H₁₅F₂N₅
• Molecular Weight: 315.3206064
• EINECS: -0
• Mol File: 1223404-88-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• PKA: 3.14±0.30(Predicted)
• CAS DataBase Reference: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine(1223404-88-3)
• EPA Substance Registry System: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine(1223404-88-3)

Safety Data

• Hazardous Substances Data: 1223404-88-3(Hazardous Substances Data)

Usage

General Description

The chemical compound "(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine" is a pyrazolo[1,5-a]pyrimidine derivative with a pyrrolidine group and difluorophenyl substituents. It is an amine compound with potential pharmaceutical applications, particularly in the field of medicinal chemistry. The compound's unique structure and functional groups make it a potentially important molecule for drug development and research into new therapeutic agents. Its specific biological and pharmacological properties would need to be further investigated and characterized for any potential pharmaceutical applications.

Upstream product

• 2646-90-4 2,5-difluorobenzaldehyde 
• 1218935-60-4 (2R)-2-(2,5-difluorophenyl)pyrrolidine hydrochloride 
• 899819-34-2 (2,5-difluorophenyl)magnesium bromide 
• 29274-24-6 5-chloropyrazolo[1,5-a]pyrimidine 
• 29274-22-4 4H,5H-pyrazolo[1,5-a]pyrimidine-5-one 
• 1919868-77-1 (R)-2-(2,5-difluorophenyl)-pyrrolidine (R)-2-hydroxy-succinate 
• 1919868-75-9 3-nitropyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 1224944-43-7 sodium pyrazolo[1,5-a] pyrimidin-5-olate 
• 1218935-59-1 (R)-(+)-2-(2,5-difluorophenyl)pyrrolidine 
• 1443623-92-4 5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole 
• 399-94-0 2-bromo-1,4-difluorobenzene 
• 1363380-51-1 5-chloro-3-nitropyrazolo[1,5-a]pyrimidine 
• 1223404-90-7 (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine 

Downstream Products

• 1223403-62-0 (R)-1-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-(4-fluorophenyl)urea 
• 1223403-61-9 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxy-3-methylazetidine-1-carboxamide 
• 1223404-67-8 (1S,4S)-N-(5-((R)-2-(2.5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxamide 
• 1223403-58-4 (3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide 
• 1223403-59-5 (3R,4R)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3,4-dihydroxypyrrolidine-1-carboxamide 
• 1223403-74-4 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-4-isopropylpiperazine-1-carboxamide 
• 1223403-60-8 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-methoxyazetidine-1-carboxamide 
• 1223403-43-7 (R)-1-tert-butyl-3-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)urea 
• 1223403-45-9 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)isobutyramide 
• 1223404-01-0 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)pivalamide 
• 1223404-82-7 (R)-methyl 2-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-ylamino)-2-oxoacetate 
• 1223403-85-7 (R)-methyl 1-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-ylcarbamoyl)cyclopropanecarboxylate 
• 1223404-13-4 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-1-(trifluoromethyl)cyclopropanecarboxamide 
• 1223404-33-8 (R)-N-(5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)pyrimidine-2-carboxamide 

Relevant articles and documents

Assignment of NMR data and Conformational analysis of larotrectinib and its precursors

NMR experiments were used to identify the two main conformations of Larotrectinib and its synthetic precursor, the nitro compound 4. Conformational analysis by dynamic NMR was performed in different temperature and solvents, combining 2D EXSY and NOE expe

Pharmaceutical compound, composition and application thereof

The invention provides a novel compound, which shows biological activity and can be used as a TRK kinase inhibitor, such as drugs for treatment of TRK-mediated diseases or symptoms and for treatment and prevention of cancers, dermatitis or asthma and the like.

Synthesis method of Larotrectinib intermediate and Larotrectinib

The invention discloses a synthesis method of Larotrectinib and a Larotrectinib intermediate. N-Boc pyrrolidone and 2,5-difluorophenyl magnesium bromide serve as raw materials, an intermediate A-1 isprepared, the intermediate A-1 is subjected to chiral catalysis hydrogenation, cyclization or first cyclization and afterwards chiral catalysis hydrogenation to obtain a chiral pyrrodlidine intermediate A-4, the intermediate A-4 and an intermediate B-3 are condensed to obtain an intermediate AB-1, the intermediate AB-1 is reduced to obtain an intermediate AB-2, the AB-2 is acylated to obtain an intermediate AB-3, and the AB-3 is subjected to a substitution reaction to obtain the target product Larotrectinib (AB-4). The intermediate A-4 with a high yield and high chiral purity is obtained through a chiral catalysis method, the B-3 with a high yield is obtained through a solvent-free one-pot method, and the Larotrectinib (AB-4) with a high yield and high purity is obtained. According to themethod, the reaction condition can also be applied to large-scale preparation, the method is suitable for industrial production, and therefore, the method has high practical values and social and economic benefits.