Trifluoroacetic acid → HCID 58508822, compound

HRID 454781Notes

Reaction equation

HRID 454781 reaction equation
FC(F)(F)C(O)=O.[NH:8]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21]C(C)(C)C)=[O:20])=[C:17]([NH:28][C:29]([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:36]=2)=[O:30])[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[NH:8]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([OH:21])=[O:20])=[C:17]([NH:28][C:29]([C:31]2[CH:32]=[N:33][CH:34]=[C:35]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:36]=2)=[O:30])[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508948HCID 58508948, compound

Product 1

HCID 58508822HCID 58508822, compound

Procedure

Trifluoroacetic acid (3.0 mL) was added to the obtained tert-butyl 4-anilino-2-(5-phenylpyridine-3-carboxamido)benzoate, followed by stirring at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and diisopropyl ether was added to the obtained residue. The solid substance was collected by filtration. Dioxane (3.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.068 mL) were sequentially added to the obtained solid substance, followed by stirring at room temperature for 1 hour and 30 minutes. A 10% aqueous solution of citric acid was added to the reaction mixture, and the solid substance was collected by filtration to obtain 73 mg of 4-anilino-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and diisopropyl ether
  2. additionwas added to the obtained residue
  3. filtrationThe solid substance was collected by filtration
  4. additionDioxane (3.0 mL) and a 2 mol/L aqueous solution of sodium hydroxide (0.068 mL) were sequentially added to the obtained solid substance
  5. stirringby stirring at room temperature for 1 hour and 30 minutes
  6. additionA 10% aqueous solution of citric acid was added to the reaction mixture
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-bc852d24e6354233a4e9169c2a209692
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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