ABT-333

Base Information

• Chemical Name: ABT-333
• CAS No.: 1132935-63-7
• Molecular Formula: C26H27N3O5S
• Molecular Weight: 493.583
• Mol file: 1132935-63-7.mol

Synonyms:ABT-333;Dasabuvir (ABT-333);N-[6-[3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide Dasabuvir (ABT-333);Dasabuvir

Chemical Property of ABT-333

Chemical Property:

• PKA: 8.52±0.30(Predicted)
• PSA: 118.90000
• Density: 1.317±0.06 g/cm3(Predicted)
• LogP: 5.58970
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99%, ^*data from raw suppliers

Dasabuvir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dasabuvir is an antiviral drug used in the treatment of chronic hepatitis C virus (HCV) infection.
• Clinical Use: Treatment of chronic hepatitis C infection
• Drug interactions: Potentially hazardous interactions with other drugsAntibacterials: avoid concomitant use with clarithromycin and telithromycin; concentration possibly reduced by rifampicin - avoid.Antidepressants: concentration possibly reduced by St John’s wort - avoid.Antiepileptics: concentration reduced by carbamazepine - avoid; concentration possibly reduced by fosphenytoin, phenobarbital, phenytoin and primidone - avoid.Antifungals: concentration of both drugs increased with ketoconazole and possibly itraconazole and posaconazole - avoid.Diuretics: concentration of furosemide increased (reduce furosemide dose).Immunosuppressants: increases concentration of ciclosporin (reduce ciclosporin dose by a fifth); everolimus (avoid); sirolimus and tacrolimus (reduce dose and use only if benefit outweighs risk - see SPC).Lipid-regulating drugs: avoid with atorvastatin, gemfibrozil and simvastatin; concentration of rosuvastatin increased (reduce dose of rosuvastatin).Oestrogens: avoid concomitant use with ethinylestradiol.

Technology Process of ABT-333

There total 20 articles about ABT-333 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.8%

methanesulfonamide (3144-09-0) + 6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (1355646-97-7) → N-(6-(3-(tert-butyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide (1132935-63-7)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; In 2-methyltetrahydrofuran; ethyl acetate; at 60 - 90 ℃; for 14h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; Large scale;

DOI:10.1021/acs.joc.8b02690

Reference yield: 84.0%

1-(3-tert-butyl-5-iodo-4-methoxyphenyl)-2,4-dihydropyrimidine-2,4(1H,3H)-dione (1132940-53-4) + N-[6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide (1132940-88-5) → N-(6-(3-(tert-butyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide (1132935-63-7)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In tetrahydrofuran; water; at 50 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.joc.8b02690

Reference yield: 74.0%

N-[6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide (1132940-88-5) + 1-(3-bromo-5-tert-butyl-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (1132942-12-1) → N-(6-(3-(tert-butyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide (1132935-63-7)

Guidance literature:

With potassium phosphate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium; In tetrahydrofuran; water; at 50 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.8b02690

upstream raw materials:

(2E)-3-methoxy-2-propenoyl isocyanate

1-(3-tert-butyl-5-iodo-4-methoxyphenyl)-2,4-dihydropyrimidine-2,4(1H,3H)-dione

N-[6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-2-yl]methanesulfonamide

1-(3-tert-butyl-5-iodo-4-methoxyphenyl )dihydropyrimidine-2,4(1H,3H)-dione

Downstream raw materials:

N-(6-(3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide monocholine salt

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