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CAS No.: | 1256387-87-7 |
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Name: | ledipasvir interMediate |
Article Data: | 9 |
Molecular Structure: | |
Formula: | N/A |
Molecular Weight: | 439.363 |
Synonyms: | (1R,3S,4S)-tert-butyl 3-(6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]iMidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate;2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-[6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benziMidazol-2-yl]-, 1,1-diMethylethyl ester, (1R,3S,4S)-;(1R,3S,4S)-3-[6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester;(1R,3S,4S)-2-tert-butyl-3-(6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[D]iMidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate;2-Azabicyclo[2.2.1]heptane-2-carboxylic acid;(1R,3S,4S)-2-tert-butyl-3-(6-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[D]iMidazol-2-yl)-2-azabicyclo[2.2.1]hept;Ledipasvir Intermediate 09;Ledipasvir Intermediate 1 |
EINECS: | -0 |
Density: | 1.21±0.1 g/cm3(Predicted) |
Boiling Point: | 613.5±35.0 °C(Predicted) |
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
bis(pinacol)diborane
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 90℃; | 94% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; for 3.5h; Inert atmosphere; | 1.16 g |
With bis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium (II) Dichloride; potassium carbonate In 1,2-dimethoxyethane Reflux; Inert atmosphere; |
(1R,3S,4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
benzene-1,4-diboronic acid bispinacol ester
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4h; Inert atmosphere; | 85% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 4h; Inert atmosphere; | 85% |
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C 2.1: ethanol / 130 - 170 °C / Sealed tube 2.2: 20 °C 3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 2: ethanol / 130 - 170 °C / Sealed tube 3: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 115 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 3.5 h / 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C 2: ethanol / 72 h / 130 - 170 °C / Sealed tube 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme |
(1R,3S,4S)-2-tert-butoxycarbonyl-3-(2-amino-4-bromophenylaminocarbonyl)-2-azabicyclo[2.2.1]heptane
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: ethanol / 130 - 170 °C / Sealed tube 1.2: 20 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: ethanol / 130 - 170 °C / Sealed tube 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C View Scheme | |
Multi-step reaction with 2 steps 1: ethanol / 72 h / 130 - 170 °C / Sealed tube 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme |
4-Bromo-benzene-1,2-diamine
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl-formamide / 1 h / 20 °C 2.1: ethanol / 130 - 170 °C / Sealed tube 2.2: 20 °C 3.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 115 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 3.5 h / 95 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 4-methyl-morpholine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C 2: ethanol / 72 h / 130 - 170 °C / Sealed tube 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 4 h / 90 °C / Inert atmosphere View Scheme |
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 6 steps 1: palladium on carbon; hydrogen / ethanol; methanol / 15 h / 30 - 35 °C / 5171.62 Torr 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C 3: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h 4: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 5: ethanol / 130 - 170 °C / Sealed tube 6: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C View Scheme |
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3.5 h / 8 - 20 °C 2: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h 3: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 4: ethanol / 130 - 170 °C / Sealed tube 5: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C View Scheme |
(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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Multi-step reaction with 4 steps 1: lithium hydroxide / methanol; tetrahydrofuran; water / 0.08 h 2: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C 3: ethanol / 130 - 170 °C / Sealed tube 4: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 90 °C View Scheme |
di-tert-butyl dicarbonate
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
Conditions | Yield |
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With dmap In dichloromethane at 20℃; for 15h; | 96.3% |
(1R,3S,4S)-3-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-dimethylethyl ester
benzyl chloroformate
Conditions | Yield |
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With dmap In dichloromethane at 20℃; for 15h; | 96% |