Toluene → HCID 86597667, compound

HRID 547753Notes

Reaction equation

HRID 547753 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1.C1(C)C=CC=CC=1>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:9])[C:26](=[O:27])[C:25]([C:20]2[CH:19]=[C:18]([Cl:17])[CH:23]=[C:22]([Cl:24])[CH:21]=2)([CH3:30])[CH3:29])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 115289412-(3,5-Dichloro-phenyl)-2-methyl-propionyl chlorideHCID 23502811[6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 86597667HCID 86597667, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1.20 g (4.74 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine and 1.43 g (5.68 mmol) 2-(3,5-dichloro-phenyl)-2-methyl-propionyl chloride in 20 ml toluene 1.27 g (10.42 mmol) 4-dimethylaminopyridine was added and the resulting solution stirred at 120° for 48 h. After cooling to ambient temperature, the solution was poured into 100 ml 0.5 N NaHCO3-solution and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, hexanes/ethyl acetate 4:1) to give 1.90 g (85%) of the title compound as a white solid.

Workup

  1. extractionextracted three times with 50 ml CH2Cl2
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash-chromatography (SiO2, hexanes/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-6e3a443b86934e809fb36e907065e3fb
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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