1132940-86-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(6-Bromonaphthalen-2-yl)methanesulfonamide is used as a key reactant in the synthesis of arylpyrimidinediones, which are known as hepatitis C virus inhibitors. The incorporation of N-(6-BroMo-naphthalen-2-yl)MethanesulfonaMide into the synthesis process allows for the development of effective antiviral agents that can target and inhibit the replication of the hepatitis C virus, providing a potential treatment option for patients suffering from this viral infection.

Upstream product

• 7499-66-3 6-Bromonaphthalen-2-amine 
• 124-63-0 methanesulfonyl chloride 
• 133277-09-5 6-bromo-2-oximino-1,2,3,4-tetrahydronaphthalene 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 4133-35-1 6-bromo-2-tetralone 
• 71590-31-3 6-bromo-2-aminonaphthalene hydrochloride 

Downstream Products

• 1132940-88-5 N-[6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide 
• 1454880-63-7 N-(6-bromo-1-(2,5-dimethylphenyl)naphthalen-2-yl)methanesulfonamide 

Relevant academic research and scientific papers

A scalable route to an unusual 3,3-dimethyl-2,3-dihydrobenzofuran ring system present in an HCV drug candidate

A scalable synthesis of a key intermediate used for the preparation of an HCV inhibitor containing an unusual dimethyldihydrobenzofuran ring is described. A key element for the successful completion of the synthesis was the correct ordering of a sequence of bromination, chlorination, and methylation to provide optimized selectivity and improved yield. A tin hydride-mediated ring closure was replaced with a more environmentally benign sulfuric acid-catalyzed Friedel-Crafts reaction. The overall yield for the preparation of the key intermediate was increased from less than 5 to 40%.

Synthesis and properties of two PRODAN-based fluorescent models of cholesterol

The syntheses and photophysical properties of 1-(5-methylhexyl)-2,3,7,8- tetrahydro-1H-naphtho[2,1-e]indol-9(6H)-one (7a) and 1-(5-methylhexyl)-2,3,8,9- tetrahydro-1H-naphtho[2,1-e]indol-6(7H)-one (7b) are reported. They are prepared in eight steps from the corresponding bromonaphthylamines. These fluorescent compounds have PRODAN-like cores, and they are structurally similar to cholesterol. Compound 7a is the first reported PRODAN derivative where both the amino and carbonyl groups are constrained to be coplanar with the naphthalene core. Comparing the photophysical behavior of these compounds with related compounds indicates that locking the amino group in a five-membered ring enhances their desirable properties as solvent polarity sensors.

Discovery and Development of Metal-Catalyzed Coupling Reactions in the Synthesis of Dasabuvir, an HCV-Polymerase Inhibitor

Dasabuvir (1) is an HCV polymerase inhibitor which has been developed as a part of a three-component direct-acting antiviral combination therapy. During the course of the development of the synthetic route, two novel coupling reactions were developed. First, the copper-catalyzed coupling of uracil with aryl iodides, employing picolinamide 16 as the ligand, was discovered. Later, the palladium-catalyzed sulfonamidation of aryl nonaflate 33 was developed, promoted by electron-rich palladium complexes, including the novel phosphine ligand, VincePhos (50). This made possible a convergent, highly efficient synthesis of dasabuvir that significantly reduced the mutagenic impurity burden of the process.

COMPOUNDS AS HEPATITIS C VIRUS (HCV) INHIBITORS AND USES THEREOF IN MEDICINE

Provided herein are compounds of Formula (I), or a stereoisomer, a geometric isomer, an enantiomer, a tautomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which are used in the treatment of HCV

ANT1VIRAL COMPOUNDS AND USES THEREOF

This invention relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

URACIL OR THYMINE DERIVATIVE FOR TREATING HEPATITIS C

Present application relates to the compounds of formula I useful to treat hepatitis C (HCV) infections. In the structure of the disclosed compounds is the uracil or thymine derivative linked via a phenylene into either fused 2-ring cyclic system (R6) or alternatively via additional two-atom linker (L) to a 5-6 membered monocycle (R6). Application further discloses polymorphs and pseudopolymorphs of two specific compounds: N-(6(3-t-butyl-5-(2>4-dioxo-3,4-dihydropyrimidin-1 (2H)- y!)2-methoxy-phenyl)naphthalen-2-yl)methanesulfonamide and (E)-N-(4(3-t- butyl-5-(2,4-dioxo-3)4-dihydropyrimidin-1 (2H)-yl)2-methoxy-styryl- phenyl)methanesulfonamide.

ANTI-INFECTIVE PYRIMIDINES AND USES THEREOF

This invention relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.