N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide

Base Information

• Chemical Name: N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide
• CAS No.: 1684386-71-7
• Molecular Formula: C₂₈H₂₃ClF₂N₄O₄
• Molecular Weight: 552.965

Synonyms:

Chemical Property of N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide

Chemical Property:

Purity/Quality:

99%+, ^*data from raw suppliers

VER-246608 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: VER-246608, is a novel pan-isoform ATP competitive inhibitor of pyruvate dehydrogenase kinase (PDK).

Technology Process of N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide

There total 14 articles about N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide 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: 18.0%

2,4-bis(benzyloxy)-N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)benzamide → N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide (1684386-71-7)

Guidance literature:

With boron trichloride; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01478

Reference yield:

2,4-bis(benzyloxy)benzoic acid (85593-77-7) → N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide (1684386-71-7)

Guidance literature:

Multi-step reaction with 5 steps

1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C

2: triethylamine / dichloromethane / 20 °C

3: trifluoroacetic acid / dichloromethane / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / acetonitrile / 1 h / 80 °C / Microwave irradiation

5: boron trichloride / dichloromethane / 4.5 h / -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; boron trichloride; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; acetonitrile;

Reference yield:

4-hydroxysalicylic acid (89-86-1) → N-[4-(2-chloro-5-methylpyrimidin-4-yl)phenyl]-N-({4-[(2,2-difluoroacetamido)methyl]phenyl}methyl)-2,4-dihydroxybenzamide (1684386-71-7)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / acetonitrile / 85 °C

2: potassium hydroxide; water / methanol / 20 - 50 °C / Reflux

3: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C

4: triethylamine / dichloromethane / 20 °C

5: trifluoroacetic acid / dichloromethane / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / acetonitrile / 1 h / 80 °C / Microwave irradiation

7: boron trichloride / dichloromethane / 4.5 h / -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; water; boron trichloride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium hydroxide; In methanol; dichloromethane; acetonitrile;

upstream raw materials:

2,4-bis(benzyloxy)benzoic acid

4-hydroxysalicylic acid

2,4-bis(benzyloxy)benzoyl chloride

benzyl 2,4-bis(benzyloxy)benzoate

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