1191237-80-5

Usage

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

• 77-76-9 2,2-dimethoxy-propane 
• 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 
• 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 academic research and scientific papers

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.

FATTY ACYL AND FATTY ETHER CONJUGATES OF REMDESIVIR AND ITS ACTIVE METABOLITES AS ANTIVIRALS

Antiviral compounds, pharmaceutical compositions containing the same, and methods of treating viral infections or medical disorders resulting from viral infections are disclosed.

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.

N-protected heterocyclic compound, preparation method thereof and method for preparing C-nucleoside derivative by using N-protected heterocyclic compound

The invention provides an N-protected heterocyclic compound, a preparation method thereof and a method for preparing a C-nucleoside derivative by using the N-protected heterocyclic compound. Specifically, the invention provides a method for preparing the C-nucleoside derivative by using a heterocyclic compound protected by N-carbobenzoxy or N-tert-butyloxycarboryl. According to the method, halogenation is not needed, temporary amino protection is not needed, protons of the heterocyclic compound are removed by directly using an organic lithium or organic magnesium compound, and addition with ribose lactone is carried out. According to the method, the synthesis route of the C-nucleoside derivative is shortened, and the yield of the reaction of the heterocyclic compound and the ribose lactone is remarkably improved under the condition that no halogen atom is used as a substituent group.

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

Method for preparing retegravir by using micro-channel reactor

The invention discloses a method for synthesizing retegravir by using a micro-channel reactor, which realizes continuous flow synthesis of retegravir by using a scale effect of a micro-flow field technology and using a novel micro-channel reactor to repla

Crystal form of nucleoside compound and preparation method thereof

The invention provides a crystal form of a nucleoside compound and a preparation method thereof, wherein the crystal form comprises a crystal form I. Crystal form . The crystal form is small in particle size, high in crystallinity and good in physical and chemical stability. The preparation method of the crystal form is simple to operate and high in repeatability.

Nucleoside compound for treating virus infection and application thereof

The invention discloses a nucleoside compound for treating coronavirus infection and a prodrug thereof, a compound shown in a formula I, the prodrug and/or pharmaceutically acceptable salt thereof, and a composition and application thereof. The compound and the composition have the application of preventing, relieving or treating coronavirus infection, or replication or reproduction of homologous variant viruses of the coronavirus infection, and cytopathic effects generated by the coronavirus infection or the replication or reproduction of the homologous variant viruses of the coronavirus infection.

Method for preparing Remdesivir key intermediate by using novel micro-channel reactor

The invention discloses a method for preparing a Remdesivir key intermediate by using a novel micro-channel reactor, which comprises the steps of simultaneously pumping a material I and a material IIinto the micro-channel reactor, conveying into a reaction module, reacting, collecting the reaction solution flowing out of the outlet of the micro-channel reactor, and carrying out after-treatment toobtain (3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2, 1-f][1,2,3]triazine-7-yl)-6-(hydroxymethyl)-2,2-dimethyl tetrahydrofuran[3,4-d] dioxazole-4-nitrile. The micro-channel reactor provided by the invention has the characteristics of low price, convenience in transportation and cleaning, high mass and heat transfer efficiency, easiness in industrial amplification and the like. The micro-channel reaction technology adopted by the invention can effectively shorten the reaction time, save the cost, can continuously produce the target product with stable quality, and is suitable for preparing the Remdesivir intermediate.

Preparation method of high-purity Remdesivir

The invention belongs to the field of medicinal chemistry, and particularly relates to a preparation method of a compound Remdesivir as shown in a formula I defined in the description. The method is simple and convenient to operate, mild in reaction condi