1191237-80-5

Basic information

• Product Name: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
• Synonyms: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile
• CAS NO: 1191237-80-5
• Molecular Weight: 331.331
• Mol File: 1191237-80-5.mol
• Article Data: 15

Chemical Properties

• Density: 1.66±0.1 g/cm3(Predicted)
• CAS DataBase Reference: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile(1191237-80-5)
• EPA Substance Registry System: (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile(1191237-80-5)

Safety Data

• Hazardous Substances Data: 1191237-80-5(Hazardous Substances Data)

Usage

Description

(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile is a complex organic compound with a unique molecular structure. It is characterized by its tetrahydrofuran and dioxole rings, as well as its triazinone and carbonitrile functional groups. (3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile is likely to have specific applications in various fields due to its unique chemical properties.

Uses

1. Used in Pharmaceutical Industry:
(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile is used as an organic synthesis intermediate for the development and production of pharmaceutical compounds, particularly Remdesivir. It plays a crucial role in the synthesis of Remdesivir, which is an antiviral medication used to treat COVID-19 and other viral infections.
2. Used in Chemical Research and Development:
(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile is also utilized as a research tool in the field of chemical research and development. Its unique structure and functional groups make it an interesting candidate for studying various chemical reactions and exploring its potential applications in different areas of chemistry.
3. Used in Organic Synthesis:
(3αR,4R,6R,6αR)-4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbonitrile can be employed as a building block in the synthesis of other complex organic molecules. Its versatile structure allows for further functionalization and modification, making it a valuable starting material for the creation of new compounds with potential applications in various industries.

Synthesis

5.62g of compound GS-441524 was dissolved in 30mL of acetone, 11.50mL of 2,2-dimethoxypropane and 1.34mL of sulfuric acid were added, stirred at 45°C for half an hour, cooled to 25°C, and the organic solvent was removed by rotary evaporation. It was extracted with 100 mL of ethyl acetate and 100 mL of saturated sodium bicarbonate aqueous solution, and the extraction was repeated three times. The ethyl acetate layers were combined, dried by adding anhydrous sodium sulfate, and filtered to remove sodium sulfate. The organic solvent was removed by rotary evaporation, and column chromatography was performed (eluent: petroleum ether/ethyl acetate (V/V)=1/2) to obtain 6.20 g of compound 5 (white solid, 97% yield).

Upstream product

• 1191237-69-0 (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 14233-64-8 (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one 
• 159326-68-8 pyrrolo[2,1-f][1,2,4]triazin-4-amine 
• 1355357-49-1 (2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile 
• 1770840-43-1 7-iodopyrrolo-[2,1-f][1,2,4]-triazin-4-amine 
• 1191237-68-9 (3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile 
• 1355049-94-3 (3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol 

Downstream Products

• 1809249-37-3 (2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 

Relevant articles and documents

PROMOIETY STRATEGY TO ENHANCE DRUG ACTIVITY

Various nucleoside phosphate and phosphonate analogues are provided for treatment of viral infections. Methods of preparing the analogues, pharmaceutical compositions containing the analogues, and methods of using the analogues as antiviral compounds, especially against adenoviruses, coronaviruses, and varicella zoster viruses, are also provided.

METHODS OF PREPARING 1'-CYANO NUCLEOSIDES

The present disclosure generally describes methods of preparing l'-cyano nucleosides, such as a compound of Formula (I). For example, the compound of Formula (I) can be prepared from a compound of Formula (Il-a) in a flow reactor.

ISOMORPHS OF REMDESIVIR AND METHODS FOR SYNTHESIS OF SAME

A new isoform of 2-ethylbutyl (2S)-2-[[[(2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3/4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate (Remdesivir) having increased water solubility is disclosed, along with methods