Dimethylformamide → HCID 86758308, compound

HRID 2227513Notes

Reaction equation

HRID 2227513 reaction equation
N1C=CC=C(C[N:8]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[C:9]2[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=O)=[CH:11][CH:10]=2)C=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[CH3:41][N:42]([CH3:45])C=O>>[N:42]1[CH:45]=[CH:12][CH:11]=[C:10]([CH2:9][NH:8][C:15](/[CH:14]=[CH:13]/[C:12]2[CH:11]=[CH:10][C:9]([N:8]([CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:20](=[O:25])[C:21]([F:22])([F:23])[F:24])=[CH:19][CH:18]=2)=[O:17])[CH:41]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 86758309HCID 86758309, compound

Product 1

HCID 86758308HCID 86758308, compoundYield 30%

Procedure

A suspension of N-(3-pyridylmethyl)-4-[(trifluoroacetyl)amino]cinnamic acid (1.55 g) and potassium carbonate (1.84 g) in 10 ml dimethylformamide was stirred with 0.7 ml t-butyl bromoacetate for 24 hours. After removal of inorganic salts by filtration, insoluble components precipitated from water were filtered off. The filtrate was extracted with ethyl acetate and the organic layer was washed with water and brine, and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give a residue, which was then separated and purified via column chromatography on silica gel (chloroform:methanol=50:1) to provide t-butyl [[4-[(E)-2-[N-(3-pyridylmethyl)carbamoyl]ethenyl]phenyl](trifluoroacetyl)amino]acetate (582 mg, 30%).

Workup

  1. customAfter removal of inorganic salts
  2. filtrationby filtration, insoluble components
  3. customprecipitated from water
  4. filtrationwere filtered off
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. customthe solvent was evaporated
  10. customto give a residue, which
  11. customwas then separated
  12. custompurified via column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-ede8ee9d461c451bb4be9b1019a016ae
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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