3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

Base Information

• Chemical Name: 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide
• CAS No.: 1150260-61-9
• Molecular Formula: C₂₃H₂₁ClF₃N₃O₃
• Molecular Weight: 479.886
• Mol file: 1150260-61-9.mol

Synonyms:3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

Chemical Property of 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

There total 6 articles about 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide 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: 76.0%

3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)benzoic acid (1150263-50-5) + (1R)-1-[1-oxido-6-(trifluoromethyl)-3-pyridinyl]ethanamine hydrochloride (1225462-34-9) → 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide (1150260-61-9)

Guidance literature:

With diethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2018.02.039

Reference yield:

(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (1149805-60-6) + 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)benzoic acid (1150263-50-5) → 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide (1150260-61-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl acetamide; N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

Reference yield:

methyl 3-bromo-5-iodobenzoate (188813-07-2) → 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide (1150260-61-9)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate; copper(l) chloride; palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 80 °C

2: palladium diacetate; trisodium tris(3-sulfophenyl)phosphine; diisopropylamine / N,N-dimethyl-formamide; water / 80 °C

3: water; sodium hydroxide / methanol

4: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylamine / N,N-dimethyl-formamide / 20 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; trisodium tris(3-sulfophenyl)phosphine; water; palladium diacetate; caesium carbonate; diethylamine; diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; copper(l) chloride; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide; 1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2018.02.039

upstream raw materials:

(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine

3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)benzoic acid

methyl 3-bromo-5-iodobenzoate

methyl 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate