55293-96-4

Usage

Uses

Used in Pharmaceutical Synthesis:
[1,2,4]Triazolo[1,5-a]pyrimidine-2-carboxaldehyde, 5,7-dimethylis used as a key intermediate in the synthesis of various pharmaceuticals due to its unique molecular structure and the presence of the carboxaldehyde group. This group allows for the formation of diverse chemical entities, making it a valuable building block in medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, [1,2,4]Triazolo[1,5-a]pyrimidine-2-carboxaldehyde, 5,7-dimethylserves as a versatile intermediate. Its 5,7-dimethyl substituents contribute to its stability and chemical reactivity, enabling the preparation of a wide range of organic compounds for various applications.
Used in Research and Development:
[1,2,4]Triazolo[1,5-a]pyrimidine-2-carboxaldehyde, 5,7-dimethylis also utilized in research and development for the exploration of new chemical reactions and the discovery of novel compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals. Its unique structure and reactivity make it an attractive candidate for studying new synthetic pathways and mechanisms.

Upstream product

• 54535-00-1 (5,7-dimethyl- [1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol 
• 63870-39-3 (5-amino-1H-[1,2,4]triazol-3-yl)-methanol; glycolate 
• 1508308-97-1 C₂₉H₃₆⁽²⁾HN₅O₃ 

Downstream Products

• 749929-33-7 2-[4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-methylpropanenitrile 
• 749929-84-8 2-[2-chloro-4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)phenyl]-2-methylpropanenitrile 
• 877131-18-5 [4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-ethylphenyl]acetonitrile 
• 877129-49-2 6-cyclopentyl-3-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-[2-(5-ethyl-4-hydroxy-2-propoxyphenyl)ethyl]-4-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 877130-28-4 filibuvir 
• 1115035-60-3 2-[4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-fluorophenyl]-2-ethylbutanenitrile 
• 749930-73-2 6-cyclopentyl-3-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-{2-[3-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]ethyl}-4-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 877131-43-6 6-cyclopentyl-3-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-6-{2-[3-ethyl-4-(hydroxymethyl)phenyl]ethyl}-4-hydroxy-5,6-dihydro-2H-pyran-2-one 
• 877131-55-0 4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)-2-ethyl-N-methylbenzamide 
• 877130-28-4 filibuvir 
• 1228897-40-2 C₂₉H₃₅N₅O₃ 
• 749931-52-0 C₂₇H₃₁ClN₄O₄ 
• 1269149-94-1 C₃₀H₃₄ClN₅O₃ 
• 1026170-39-7 C₂₉H₃₅ClN₄O₄ 

Relevant academic research and scientific papers

Synthesis of filibuvir. Part III. Development of a process for the reductive coupling of an aldehyde and a β-keto-lactone

Development of a reductive coupling of a β-keto-lactone and an aldehyde is described, in which the Hantzsch ester serves as an inexpensive and convenient reducing agent. Structural features in the β-keto-lactone rendered standard reductive coupling conditions ineffective, requiring development of a specific addition and temperature protocol. Identification of one of the reactants as Ames positive required a single-digit parts per million control strategy for this impurity in the final active pharmaceutical ingredient (API).

INHIBITORS OF HEPATITIS C VIRUS POLYMERASE

The present invention provides, among other things, compounds represented by the general Formula (I) and pharmaceutically acceptable salts thereof, wherein X, Y, R1A, R1B, R2, and R3 are as defined in classes and subclasses herein and compositions (e.g., pharmaceutical compositions) comprising such compounds, which compounds are useful as inhibitors of hepatitis C virus polymerase, and thus are useful, for example, as medicaments for the treatment of HCV infection.

METHODS FOR THE PREPARATION OF HCV POLYMERASE INHIBITORS

The present invention relates to methods and compounds useful in the preparation of compounds of the formula (I).

Development of a synthetic process towards a hepatitis C polymerase inhibitor

The synthesis of 2-(4-{2-[(2R)-2-Cyclopentyl-5-(5,7-dimethyl-[1,2,4] triazolo[1,5-a]pyrimidin-2-ylmethyl)-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl] -ethyl}-2-fluoro-phenyl)-2-methyl-propionitrile (1) on multikilogram scale is described. Initial synthesis

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same

The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1 and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula 1, and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula 1. The invention also relates to methods of preparing the compounds of formula 1.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The invention relates to compounds of the formula (I) and to pharmaceutically acceptable salts, solvates, prodrugs and metabolites thereof, wherein W, Z, R1and R2, are as defined herein. The invention also relates to methods of treating Hepatitis C virus in mammals by administering the compounds of formula (I), and to pharmaceutical compositions for treating such disorders, which contain the compounds of formula (I). The invention also relates to methods of preparing the compounds of formula (I).