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1132935-63-7

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Basic Information
CAS No.: 1132935-63-7
Name: ABT-333
Article Data: 5
Molecular Structure:
Molecular Structure of 1132935-63-7 (ABT-333)
Formula: C26H27N3O5S
Molecular Weight: 493.583
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
Density: 1.317±0.06 g/cm3(Predicted)
PSA: 118.90000
LogP: 5.58970
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1132935-63-7

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

Conditions
ConditionsYield
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;90.8%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos In tetrahydrofuran at 20 - 90℃; for 20h; Product distribution / selectivity; Inert atmosphere;
1132940-53-4

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

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

1132935-63-7

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

Conditions
ConditionsYield
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; Suzuki Coupling; Inert atmosphere;84%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water Inert atmosphere; Large scale;76.5%
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In ethanol; water; toluene at 100℃; for 1.33333h; Product distribution / selectivity; Suzuki Coupling; Microwave irradiation;25%
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℃; Product distribution / selectivity; Suzuki Coupling;
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℃; Product distribution / selectivity; Suzuki Coupling;
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N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)methanesulfonamide

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1132935-63-7

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

Conditions
ConditionsYield
With potassium phosphate; dichloro[1,1′-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P′]palladium In tetrahydrofuran; water at 50℃; for 16h; Suzuki Coupling; Inert atmosphere;74%
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1132935-63-7

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

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In tert-Amyl alcohol at 90℃; for 18h; Inert atmosphere;0.9%

C22H26N2O3S

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1132935-63-7

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

Conditions
ConditionsYield
Stage #1: C22H26N2O3S; (2E)-3-methoxy-2-propenoyl isocyanate In N,N-dimethyl-formamide at -25 - 20℃; for 2h;
Stage #2: With sulfuric acid In ethanol; water at 100℃; for 16h; Product distribution / selectivity;
1132940-49-8

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

1132940-88-5

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

1132935-63-7

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

Conditions
ConditionsYield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ethanol; water; toluene at 100℃; for 1h; Product distribution / selectivity; Suzuki Coupling; Microwave irradiation;

C27H31N3O6S

1132935-63-7

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

Conditions
ConditionsYield
With ethanol; sulfuric acid; water at 100℃; for 16h; Product distribution / selectivity;
88-18-6

2-tert-Butylphenol

1132935-63-7

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium hydroxide / methanol / 20 °C
2.1: sodium iodide; sodium hypochlorite / methanol / 0 °C
2.2: 1.62 h / 1.2 - 4.1 °C / pH 3
3.1: sodium hydroxide / water; acetone
4.1: potassium phosphate; copper(l) iodide / N-(2-cyanophenyl)pyridine-2-carboxamide / acetonitrile; dimethyl sulfoxide / 16 h / 60 °C / Inert atmosphere
5.1: 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 / water; tetrahydrofuran / 2.5 h / 65 °C / Inert atmosphere
6.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere
7.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / tetrahydrofuran / 20 h / 20 - 90 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol / 20 °C
1.2: 0 °C
2.1: potassium phosphate; copper(l) iodide; N-(2-cyanophenyl)pyridine-2-carboxamide / dimethyl sulfoxide / 16 h / 60 °C / Inert atmosphere
3.1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / methanol / 20 °C
1.2: 0 °C
2.1: potassium phosphate; copper(l) iodide; 2-(2'-pyridyl)benzimidazole / dimethyl sulfoxide / 24 h / 80 °C / Inert atmosphere
3.1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydroxide / methanol / 20 °C
1.2: 0 °C
2.1: potassium phosphate; copper(l) iodide; N-(2-cyanophenyl)pyridine-2-carboxamide / dimethyl sulfoxide / 16 h / 60 °C / Inert atmosphere
3.1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 1.25 h / 60 - 65 °C / Inert atmosphere; Large scale
4.1: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 1.25 h / 30 °C / Large scale
5.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / 2-methyltetrahydrofuran; ethyl acetate / 14 h / 60 - 90 °C / Inert atmosphere; Sealed tube; Large scale
View Scheme
Multi-step reaction with 5 steps
1.1: sodium hydroxide / methanol / 20 °C
1.2: 0 °C
2.1: potassium phosphate; copper(l) iodide; 2-(2'-pyridyl)benzimidazole / dimethyl sulfoxide / 24 h / 80 °C / Inert atmosphere
3.1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 1.25 h / 60 - 65 °C / Inert atmosphere; Large scale
4.1: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 1.25 h / 30 °C / Large scale
5.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / 2-methyltetrahydrofuran; ethyl acetate / 14 h / 60 - 90 °C / Inert atmosphere; Sealed tube; Large scale
View Scheme
173194-95-1

(6-hydroxynaphthalen-2-yl)boronic acid

1132935-63-7

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 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 / water; tetrahydrofuran / 2.5 h / 65 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere
3: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / tetrahydrofuran / 20 h / 20 - 90 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 1.25 h / 60 - 65 °C / Inert atmosphere; Large scale
2: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 1.25 h / 30 °C / Large scale
3: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / 2-methyltetrahydrofuran; ethyl acetate / 14 h / 60 - 90 °C / Inert atmosphere; Sealed tube; Large scale
View Scheme
1132940-53-4

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

1132935-63-7

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 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 / water; tetrahydrofuran / 2.5 h / 65 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere
3: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / tetrahydrofuran / 20 h / 20 - 90 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: potassium phosphate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; tris-(dibenzylideneacetone)dipalladium(0) / water; tetrahydrofuran / 1.25 h / 60 - 65 °C / Inert atmosphere; Large scale
2: potassium carbonate / N,N-dimethyl-formamide; acetonitrile / 1.25 h / 30 °C / Large scale
3: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos / 2-methyltetrahydrofuran; ethyl acetate / 14 h / 60 - 90 °C / Inert atmosphere; Sealed tube; Large scale
View Scheme
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