1223404-90-7

Basic information

• Product Name: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine
• Synonyms: Larotrectinib DFP-PNPP Impurity;Larotrectinib Impurity 3（Larotrectinib DFP-PNPP Impurity）;(R)-5-(2-(2,5-Difluorophenyl)-1-pyrrolidinyl)-3-nitropyrazolo[1,5-a]pyrimidine;(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine;(2R)-2-(2,5-difluorophenyl)-1-{3-nitropyrazolo[1,5-a]pyrimidin-5-yl}pyrrolidine;5-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]-3-nitr opyrazolo[1,5-a]pyrimidine;Pyrazolo[1,5-a]pyrimidine, 5-[(2R)-2-(2,5-difluorophenyl)-1-pyrrolidinyl]-3-nitro-
• CAS NO: 1223404-90-7
• Molecular Formula: C₁₆H₁₃F₂N₅O₂
• Molecular Weight: 345.3
• Mol File: 1223404-90-7.mol

Chemical Properties

• Appearance: /
• Density: 1.58±0.1 g/cm3(Predicted)
• PKA: -0.73±0.40(Predicted)
• CAS DataBase Reference: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine(1223404-90-7)
• EPA Substance Registry System: (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine(1223404-90-7)

Safety Data

• Hazardous Substances Data: 1223404-90-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-5-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine is used as a potential pharmaceutical candidate for its possible receptor binding or enzyme inhibition properties. The presence of the difluorophenyl and pyrrolidinyl groups, along with its chiral R-configuration, may contribute to its bioactivity and selectivity in targeting specific biological pathways.
Used in Drug Discovery Research:
In the field of drug discovery, (R)-5-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine serves as a valuable compound for research and development. Its unique structure and potential biological activity make it a promising candidate for further investigation into its therapeutic potential, including its interaction with biological systems and its effects on various diseases.

Upstream product

• 1223404-89-4 (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine 
• 1919868-75-9 3-nitropyrazolo[1,5-a]pyrimidin-5(4H)-one 
• 1363380-51-1 5-chloro-3-nitropyrazolo[1,5-a]pyrimidine 
• 1919868-77-1 (R)-2-(2,5-difluorophenyl)-pyrrolidine (R)-2-hydroxy-succinate 
• 399-94-0 2-bromo-1,4-difluorobenzene 
• 1443623-92-4 5-(2,5-difluorophenyl)-3,4-dihydro-2H-pyrrole 
• 1919868-77-1 (R)-(+)-2-(2,5-difluorophenyl)pyrrolidine (R)-2-hydroxysuccinate 
• 1218935-59-1 (R)-(+)-2-(2,5-difluorophenyl)pyrrolidine 
• 2646-90-4 2,5-difluorobenzaldehyde 
• 29274-22-4 4H,5H-pyrazolo[1,5-a]pyrimidine-5-one 
• 29274-24-6 5-chloropyrazolo[1,5-a]pyrimidine 
• 899819-34-2 (2,5-difluorophenyl)magnesium bromide 
• 1218935-60-4 (2R)-2-(2,5-difluorophenyl)pyrrolidine hydrochloride 

Downstream Products

• 1223404-88-3 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-amine 
• 2135871-21-3 phenyl (5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate 
• 1223405-08-0 (S)-N-(5-((R)-2-(2,5-difluorophenyl)-pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide hydrogen sulfate 
• 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 

Relevant articles and documents

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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.

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PREPARATION OF (S)-N-(5-((R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDIN-1-YL)PYRAZOLO[1,5-A]PYRIMIDIN-3-Y L)-3-HYDROXYPYRROLIDINE-1-CARBOXAMIDE

Process for preparing (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-l- yl)pyrazolo[l,5-a] pyrimidin-3-yl)-3-hydroxypyrrolidine-l-carboxamide (formula I) or a salt thereof by reacting phenyl(5-((R)-2-(2,5- difluorophenyl)pyrrolidin-l-yl)-3,3a-dihydropyrazolo[l,5-a]pyrimidin-3- yl)carbamate or a similar derivative (formula 13) with (S)-pyrrolidin-3- ol (formula 14). Process for preparing phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-l- yl)-3,3a-dihydropyrazolo[l,5-a]pyrimidin-3-yl)carbamate (formula 13) or a similar derivative by reduction of (R)-5-(2-(2,5-difluorophenyl) pyrrolidin-l-yl)-3-nitropyrazolo[l,5-a]pyrimidine (formula 11) to (R) -5-(2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazolo[l,5-a]pyrimidin-3- amine (formula 12). Process for preparing (R)-2-(2,5-difluorophenyl)pyrrolidine(R) -2-hydroxysuccinate (formula 10) by treating (R)-N-((R)-l-(2,5- difluorophenyl)-3-(l,3-dioxan-2-yl)propyl)-2-methylpropane-2- sulfinamide (formula 19) with an acid and a reducing agent. (S)-N-(5-((R)-2-(2,5-difluorophenyl)-pyrrolidin-l-yl)-pyrazolo[l,5- a]pyrimidin-3-yl)-3-hydroxypyrrolidine-l-carboxamide, is a tyrosin kinase (TRK) inhibitor for trearing e.g. cancer.