Ethyl Acetate → 4-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-N-(2-pyridylmethyl)benzoic acid amide

HRID 645301

Reaction equation

HRID 645301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:22]([F:25])([F:24])[F:23])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][NH2:33].[Cl-].C(N(CC)CCCN=C=NCC)C.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:22]([F:25])([F:24])[F:23])=[CH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:33][CH2:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=3)=[O:18])=[CH:20][CH:21]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 195092-PyridinemethanamineHCID 667356584-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acidHCID 866264281-(3-(Diethylamino)propyl)-3-ethylcarbodiimide chloride

Product 1

HCID 667353614-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-N-(2-pyridylmethyl)benzoic acid amideYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid that was synthesized under Synthetic Example 4 and 0.21 g of 2-picolylamine in 6 mL of N,N-dimethylformamide, 0.32 g of 1-(3-(diethylamino)propyl)-3-ethylcarbodiimide chloride was added at room temperature and the mixture was stirred for 72 hours. After the completion of reaction, 20 mL of ethyl acetate and 15 mL of saturated saline were added to the reaction solution, the mixture was separated to extract an aqueous layer with 10 mL of ethyl acetate whereto an organic layer was added, the resulting mixture was washed with 10 mL of water and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After purification of the resulting residue using silica gel column chromatography that was eluted with ethyl acetate-hexane (5:1) to obtain 0.17 g of aimed product as resinous matter.

Workup

  1. additionwas added at room temperature
  2. additionwere added to the reaction solution
  3. customthe mixture was separated
  4. extractionto extract an aqueous layer with 10 mL of ethyl acetate whereto an organic layer
  5. additionwas added
  6. washthe resulting mixture was washed with 10 mL of water
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customAfter purification of the resulting residue
  10. washwas eluted with ethyl acetate-hexane (5:1)

Sources & evidence

ORD record
ord-6fdbcdd4e796477d9300a9ac0b405854
Source dataset
uspto-grants-2010_04
Patent number
US07700808B2

Linked notes

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