3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester

Base Information

• Chemical Name: 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester
• CAS No.: 914944-26-6
• Molecular Formula: C₂₅H₂₃F₄N₅O₅
• Molecular Weight: 549.482
• Mol file: 914944-26-6.mol

Synonyms:3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester

Chemical Property of 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester

There total 21 articles about 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester 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: 52.0%

3-((6-amino-4-(tert-butyloxycarbonyl(methyl)amino)-1-methyl-1H-imidazo[4,5-c]pyridine-7-yl)ethynyl)-5-fluorobenzoic acid methyl ester (914944-25-5) + trifluoroacetic anhydride (407-25-0) → 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester (914944-26-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.333333h;

Reference yield:

2,4,6-trichloropyridine (16063-69-7) → 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester (914944-26-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: ethanol / 1.66 - 24 h / 20 - 60 °C

2.1: sulfuric acid; nitric acid / 0.92 h / 0 - 6 °C

3.1: ammonium chloride / iron / water / 2 h / 20 - 90 °C

4.1: ethanol / 15 h / 20 - 80 °C

5.1: ethanol / 3 - 24 h / 82 - 120 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.58 - 1 h / -78 - -20 °C

6.2: 3.5 - 16 h / -20 - 20 °C

7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl acetamide / 5 - 8.33 h / 110 - 115 °C

8.1: hydrogenchloride / tetrahydrofuran; water / 0.33 - 0.5 h / 0 - 5 °C

8.2: pH 12

9.1: N-iodo-succinimide / acetonitrile / 2.25 h / 0 °C / Cooling with ethanol-dry ice

10.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 90 °C

11.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C

With hydrogenchloride; N-iodo-succinimide; sulfuric acid; nitric acid; sodium hexamethyldisilazane; ammonium chloride; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iron; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; water; acetonitrile;

Reference yield:

3-bromo-5-fluorobenzoic acid (176548-70-2) → 3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester (914944-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hexane; dichloromethane / 0.5 h / 20 °C

2.1: triethylamine / bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾ / toluene

2.2: 0.5 h / 95 °C

3.1: potassium hydroxide / methanol; water / 0.5 h

4.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 90 °C

5.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C

With potassium hydroxide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; In methanol; hexane; dichloromethane; water; toluene;

upstream raw materials:

3-((6-amino-4-(tert-butyloxycarbonyl(methyl)amino)-1-methyl-1H-imidazo[4,5-c]pyridine-7-yl)ethynyl)-5-fluorobenzoic acid methyl ester

trifluoroacetic anhydride

3-bromo-5-fluorobenzoic acid

methyl 3-bromo-5-fluoro-benzoate

Downstream raw materials:

3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid

3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester

Refernces