160616-03-5

Basic information

• Product Name: Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-
• Synonyms: Benzamide,N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl];(R)-9-(2-hydroxypropyl)-N6-benzoyladenine
• CAS NO: 160616-03-5
• Molecular Formula: C15H15N5O2
• Molecular Weight: 297.316
• Mol File: 160616-03-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 223°C
• Density: 1.40±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-(160616-03-5)
• EPA Substance Registry System: Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]-(160616-03-5)

Safety Data

• Hazardous Substances Data: 160616-03-5(Hazardous Substances Data)

Usage

Description

Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]is a complex organic compound with a specific molecular structure that features a benzamide group attached to a 9H-purin-6-yl moiety with a 2-hydroxypropyl chain in the R configuration. Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]is characterized by its unique chemical properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Benzamide, N-[9-[(2R)-2-hydroxypropyl]-9H-purin-6-yl]is used as a key intermediate in the synthesis of phosphonomethoxypropyl acyclic nucleotide analogs. These analogs are important for the development of new drugs targeting various diseases, including viral infections and cancer, due to their ability to interfere with nucleotide metabolism and other cellular processes.
The compound's unique structure allows it to be a valuable building block in the creation of novel therapeutic agents, making it a promising candidate for further research and development in the pharmaceutical industry. Its role in the preparation of acyclic nucleotide analogs highlights its potential in contributing to the advancement of medical treatments and improving patient outcomes.

Upstream product

• 98-88-4 benzoyl chloride 
• 14047-28-0 (R)-9-(2-hydroxypropyl)adenine 
• 160616-02-4 (R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 

Downstream Products

• 627510-49-0 [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester 
• 147127-20-6 tenofovir 

Relevant articles and documents

SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH

The (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives) exhibit very high activity against retroviruses.This paper describes the synthesis of enantiomeric 9-(2-phosphonomethoxypropyl)adenines (I and XXVII), 9-(2-phosphonomethoxypropyl)-2,6-diaminopurines (II and XXXI), 9-(2-phosphonomethoxypropyl)guanines (III and XXIX) and 1-(R)-(2-phosphonomethoxypropyl)cytosine (XIX) by alkylation of N-protected N-(2-hydroxypropyl) derivatives of the corresponding bases with bis(2-propyl) p-toluenesulfonyloxymethylphosphonate (X), followed by stepwise N- and O-deprotection of the intermediates.The key intermediates, N-(2-hydropxypropyl) derivatives IX and XXV, were obtained by alkylation of the appropriate heterocyclic base with (R)- or (S)-2-(2-tetrahydropyranyloxy)propyl p-toluenesulfonate (VII or XXIII) ans acid hydrolysis of the resulting N- derivatives VIII and XXII.The chiral synthons were prepared by tosylation of (R)- or (S)-2-(2-tetrahydropyranyloxy)propanol (VI or XXI) available by reduction of enantiomeric alkyl 2-O-tetrahydropyranyllactates V and XXI with sodium bis(2-methoxyethyoxy)aluminum hydride.This approach was used for the synthsis of cytosine, adenine and 2,6-diaminopurine derivatives, while compounds derived from guanine were prepared by hydrolysis of 2-amino-6-chloropurine intermediates.Cytosine derivative IXe was also synthesized by alkylation of 4-methoxy-2-pyrimidone followed by ammonolysis of the intermediate IXf.