ledipasvir interMediate CAS 1256387-87-7

Introduction：Basic information about ledipasvir interMediate CAS 1256387-87-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

ledipasvir interMediate Basic information

• Product Name: ledipasvir interMediate
• Synonyms: IdentificationName (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;tert-butyl (1R,3S,4S)-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;(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);(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;Identification Name (1R,3S,4S)-3-[6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-;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]hept
• CAS: 1256387-87-7
• MF: C24H34BN3O4
• MW: 439.36
• EINECS: 1592732-453-0
• Mol File: 1256387-87-7.mol

ledipasvir interMediate Chemical Properties

• Boiling point: 613.5±35.0 °C(Predicted)
• density: 1.21±0.1 g/cm3(Predicted)
• storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
• pka: 12.16±0.10(Predicted)
• Appearance: Off-white to light yellow Solid
• InChIKey: MYPUONINDNZBTH-GMBSWORKSA-N
• SMILES: [C@]12([H])C[C@]([H])(CC1)[C@@H](C1NC3=CC(B4OC(C)(C)C(C)(C)O4)=CC=C3N=1)N2C(OC(C)(C)C)=O

ledipasvir interMediate Usage And Synthesis

Synthesis

1256387-74-2

99770-93-1

1256387-87-7

I. Preparation of Compound 613: tert-Butyl (1R,3S,4S)-3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (264 mg, 0.673 mmol), bis(pinacol) 1,4-phenylene diboronate (5 eq, 3.36 g, 6.95 mmol), tetrakis(triphenylphosphine) A mixture of palladium (5%, 39 mg) and 2M aqueous potassium carbonate (3 eq, 1.01 mL) in 5 mL of 1,2-dimethoxyethane (DME) was heated to 90°C for 4 hours under argon protection. After completion of the reaction, the reaction mixture was cooled, diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by fast column chromatography (silica gel, 20% to 60% ethyl acetate/hexane gradient elution) to afford (1R,3S,4S)-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-carboxylic acid tert-butyl ester (295 mg, 85% yield).LCMS-ESI (m/z): [M+H]+ Calculated value C30H38BN3O4: 515.45; Measured value: 516.1.

References

[1] Patent: WO2013/40492, 2013, A2. Location in patent: Page/Page column 91-92
[2] Patent: US2013/273005, 2013, A1. Location in patent: Paragraph 0350

ledipasvir interMediate Preparation Products And Raw materials

• Raw materials: 2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-(6-broMo-1H-benziMidazol-2-yl)-, 1,1-diMethylethyl ester,(1R,3S,4S)--->1,4-Benzenediboronic acid bis(pinacol) ester-->Bis(pinacolato)diboron-->Tetrakis(triphenylphosphine)palladium-->Potassium carbonate-->Water-->1,2-Dimethoxyethane