HCID 68958430, compound → HCID 57668091, compound

HRID 2191789Notes

Reaction equation

HRID 2191789 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([NH:6][C:7]2[CH:19]=[C:18](/[CH:20]=[CH:21]/[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:23]=3)[CH:17]=[CH:16][C:8]=2[C:9]([O:11]C(C)(C)C)=[O:10])=[CH:4][CH:3]=1>[C].[Pd].C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]2[CH:19]=[C:18]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH:23]=3)[CH:17]=[CH:16][C:8]=2[C:9]([OH:11])=[O:10])=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 68958430HCID 68958430, compound

Product 1

HCID 57668091HCID 57668091, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

Acetic acid 2.0 mL,dioxane 2.0 mL and 10% palladium-carbon 37 mg were added to the obtained tert-butyl 2-(4-fluoroanilino)-4-((E)-2-(3-(methanesulfonamido)phenyl)vinyl)benzoate sequentially, and it was stirred under hydrogen atmosphere at room temperature for 5 hours and 30 minutes. 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 2-(4-fluoroanilino)-4-(2-(3-(methanesulfonamido)phenyl)ethyl)benzoic acid 75 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-10cd70aa91974bcaa27a3cdf4588fe76
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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