HCID 68957316, compound → HCID 68959410, compound

HRID 2191787Notes

Reaction equation

HRID 2191787 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[CH:25]=[CH:24][C:16]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>[C].[Pd].C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][C:13]2[CH:25]=[CH:24][C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH:14]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 68957316HCID 68957316, compound

Product 1

HCID 68959410HCID 68959410, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To the obtained tert-butyl 4-((E)-2-(4-(acetamido)phenyl)vinyl)-2-(4-fluoroanilino)benzoate were added acetic acid 2.0 mL,dioxane 2.0 mL and 10% palladium-carbon 30 mg sequentially, and it was stirred under hydrogen atmosphere at room temperature for 3 hours. The solvent was removed under reduced pressure after insoluble matter was filtrated. Trifluoroacetic acid 10 mL was added to the obtained residue, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure,diisopropyl ether was added to the obtained residue, and solid matter was filtrated to give 4-(2-(4-(acetamido)phenyl)ethyl)-2-(4-fluoroanilino)benzoic acid 60 mg of a white solid.

Workup

  1. customThe solvent was removed under reduced pressure after insoluble matter
  2. filtrationwas filtrated
  3. additionTrifluoroacetic acid 10 mL was added to the obtained residue, and it
  4. stirringwas stirred at room temperature for 2 hours
  5. customThe solvent was removed under reduced pressure,diisopropyl ether
  6. additionwas added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-072e61ca876d4884a28e3fdef2c800ab
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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