6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide

Base Information

• Chemical Name: 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide
• CAS No.: 1012792-57-2
• Molecular Formula: C₁₈H₁₈Cl₂N₂O₂
• Molecular Weight: 365.259
• Mol file: 1012792-57-2.mol

Synonyms:6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide

Chemical Property of 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide

There total 5 articles about 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide 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: 73.0%

6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid (1012792-56-1) + (1R,2R)-trans-2-aminocyclohexanol hydrochloride (13374-31-7) → 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide (1012792-57-2)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

Reference yield:

5-bromo-6-hydroxy-3-pyridinecarboxylic acid (41668-13-7) → 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide (1012792-57-2)

Guidance literature:

Multi-step reaction with 5 steps

1: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

2: dichloromethane / 1.25 h / 70 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; water / 1 h / 90 °C / Inert atmosphere

4: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / Inert atmosphere; Reflux

5: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With quinoline; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; lithium hydroxide monohydrate; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm4010708

Reference yield:

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → 6-chloro-5-(4-chlorophenyl)-N-[(1R,2R)-2-hydroxycyclohexyl]-3-pyridine carboxamide (1012792-57-2)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid; bromine / 18.75 h / 45 - 50 °C / Inert atmosphere

2: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

3: dichloromethane / 1.25 h / 70 °C / Inert atmosphere

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; water / 1 h / 90 °C / Inert atmosphere

5: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / Inert atmosphere; Reflux

6: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

With quinoline; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; lithium hydroxide monohydrate; bromine; sodium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm4010708

upstream raw materials:

6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

(1R,2R)-trans-2-aminocyclohexanol hydrochloride

5-bromo-6-hydroxy-3-pyridinecarboxylic acid

6-hydroxy-3-pyridinecarboxylic acid

Refernces

• 1、 -. "5-PHENYL-NICOTINAMIDE DERIVATIVES". Page/Page column 11. . Retrieved 2008/06/13.