3-Methyl-n-(1-oxy-3',4',5',6'-tetrahydro-2'h-(2,4'-bipyridine)-1'-ylmethyl)benzamide

Base Information

• Chemical Name: 3-Methyl-n-(1-oxy-3',4',5',6'-tetrahydro-2'h-(2,4'-bipyridine)-1'-ylmethyl)benzamide
• CAS No.: 630119-43-6
• Molecular Formula: C19H23N3O2
• Molecular Weight: 325.411
• UNII: 4L6071XH2J
• ChEMBL ID: CHEMBL219182
• DSSTox Substance ID: DTXSID30212235
• Pharos Ligand ID: 6L9KR8XWAAG2
• Wikidata: Q4650423
• Wikipedia: ABT-670
• Mol file: 630119-43-6.mol

Synonyms:3-methyl-N-(1-oxy-3',4',5',6'-tetrahydro-2'H-(2,4'-bipyridine)-1'-ylmethyl)benzamide;ABT 670;ABT-670;ABT670

Chemical Property of 3-Methyl-n-(1-oxy-3',4',5',6'-tetrahydro-2'h-(2,4'-bipyridine)-1'-ylmethyl)benzamide

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 325.17902698
• Heavy Atom Count: 24
• Complexity: 409

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C(=O)NCN2CCC(CC2)C3=CC=CC=[N+]3[O-]

Technology Process of 3-Methyl-n-(1-oxy-3',4',5',6'-tetrahydro-2'h-(2,4'-bipyridine)-1'-ylmethyl)benzamide

There total 8 articles about 3-Methyl-n-(1-oxy-3',4',5',6'-tetrahydro-2'h-(2,4'-bipyridine)-1'-ylmethyl)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: 85.0%

1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] N-oxide hydrochloride + formaldehyd (50-00-0,30525-89-4,61233-19-0) + m-toluamide (618-47-3) → 2-(1-{[(3-methylbenzoyl)amino]methyl}-4-piperidinyl)pyridinium N-oxide (630119-43-6)

Guidance literature:

1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] N-oxide hydrochloride; With potassium carbonate; In 1,4-dioxane; toluene; at 20 ℃; for 0.5h;

formaldehyd; m-toluamide; In 1,4-dioxane; toluene; at 80 ℃; for 4h;

DOI:10.1021/jm060662k

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + m-toluamide (618-47-3) → 2-(1-{[(3-methylbenzoyl)amino]methyl}-4-piperidinyl)pyridinium N-oxide (630119-43-6)

Guidance literature:

1',2',3',4',5',6'-hexahydro-2'H-[2,4'-bipyridine] N-oxide hydrochloride; With potassium carbonate; In 1,4-dioxane; toluene; at 20 ℃; for 0.5h;

formaldehyd; m-toluamide; In 1,4-dioxane; water; toluene; at 20 - 80 ℃; for 4h;

Reference yield:

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 2-(1-{[(3-methylbenzoyl)amino]methyl}-4-piperidinyl)pyridinium N-oxide (630119-43-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 68 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

2.1: 64 percent / Pd(PPh₃)4 / tetrahydrofuran / 1.5 h / 60 °C

3.1: 99 percent / H₂ / Pd/C / 1.5 h / 20 °C / 3102.89 Torr

4.1: 72 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2.5 h / 0 - 20 °C

5.1: 99 percent / HCl(gas) / ethyl acetate / 0.25 h / -78 °C

6.1: K₂CO₃ / toluene; dioxane / 0.5 h / 20 °C

6.2: 85 percent / toluene; dioxane / 4 h / 80 °C

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; hydrogen; potassium carbonate; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate; toluene; 2.1: Negishi cross-coupling;

DOI:10.1021/jm060662k

upstream raw materials:

formaldehyd

m-toluamide

1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-carboxylic acid tert-butyl ester

N-tert-butyloxycarbonylpiperidin-4-one