[(4-Iodophenyl)sulfonyl]-2-pyridylamine → 2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acid

HRID 1653898Notes

Reaction equation

HRID 1653898 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:15])=[C:7]([CH:14]=1)[C:8]([O:10]C(C)C)=[O:9])=[CH2:2].I[C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>>[OH:15][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[CH:2][C:17]2[CH:18]=[CH:19][C:20]([S:23]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:14][C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 2

HCID 1143526[(4-Iodophenyl)sulfonyl]-2-pyridylamineHCID 19423367Isopropyl 5-ethenyl-2-hydroxybenzoate

Product 1

HCID 543430162-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]ethenyl]benzoic acidYield 40%

Procedure

Isopropyl 5-ethenyl-2-hydroxybenzoate was reacted with 4-iodo-N-(2-pyridinyl)benzenesulfonamide similarly to the procedure of Example 5c. After the reaction, the solvent was evaporated, toluene was added and the suspension filtered and washed with toluene. After drying on the filter and washing with water the material was hydrolyzed and precipitated similarly to the procedure of Example 3c. Yield 40%.

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. additiontoluene was added
  4. filtrationthe suspension filtered
  5. washwashed with toluene
  6. customAfter drying on the
  7. filtrationfilter
  8. washwashing with water the material
  9. customprecipitated similarly to the procedure of Example 3c

Sources & evidence

ORD record
ord-bba47e46358c4e698f580bb1a76d12eb
Source dataset
uspto-grants-1995_04
Patent number
US05403930

Reaction notes

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