Ethanolamine → N-[4-(2-Chloro-phenyl)-6-(2-hydroxy-ethylamino)-pyridin-3-yl]-2-(3,5-dichloro-phenyl)-N-methyl-isobutyramide

HRID 1951662Notes

Reaction equation

HRID 1951662 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1.[CH2:30]([CH2:32][NH2:33])[OH:31]>C([O-])(O)=O.[Na+]>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:4]1[CH:3]=[C:2]([NH:33][CH2:32][CH2:30][OH:31])[N:7]=[CH:6][C:5]=1[N:8]([CH3:22])[C:9](=[O:21])[C:10]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=1)([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 86597667HCID 86597667, compound

Product 1

HCID 11283284N-[4-(2-Chloro-phenyl)-6-(2-hydroxy-ethylamino)-pyridin-3-yl]-2-(3,5-dichloro-phenyl)-N-methyl-isobutyramideYield 54%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 0.14 g (0.29 mmol) N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-2-(3,5-dichloro-phenyl)-N-methyl-isobutyramide and 4 ml ethanolamine was stirred at 130° for 9 h. After cooling to ambient temperature, the solution was poured into 20 ml 0.5N NaHCO3-solution and extracted three times with 30 ml CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by flash-chromatography (SiO2, CH2Cl2/ethyl acetate 1:3) to give 0.08 g (54%) of the title compound as a white foam.

Workup

  1. extractionextracted three times with 30 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, CH2Cl2/ethyl acetate 1:3)

Sources & evidence

ORD record
ord-927404ac80f34907b6bedc9cc180345d
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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