Trifluoroacetic acid → HCID 58508708, compound

HRID 454737Notes

Reaction equation

HRID 454737 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[CH:15]=[C:16]([C:20]([NH:22][C:23]3[CH:35]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH:33]=[CH:32][C:24]=3[C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH:17]=[N:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[C:8]1([C:14]2[CH:15]=[C:16]([C:20]([NH:22][C:23]3[CH:35]=[C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH:33]=[CH:32][C:24]=3[C:25]([OH:27])=[O:26])=[O:21])[CH:17]=[N:18][CH:19]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58508791HCID 58508791, compound

Product 1

HCID 58508708HCID 58508708, compoundYield 65%

Procedure

Trifluoroacetic acid (4.0 mL) was added to the obtained tert-butyl 2-(5-phenylpyridine-3-carboxamido)-4-(pyridin-2-yl)benzoate (0.13 g), followed by stirring at room temperature for 1 hour. 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 (0.19 mL) were added to the obtained solid, followed by stirring at room temperature for 1 hour. A 10% aqueous solution of citric acid and ethyl acetate were added to the reaction mixture, and the solid substance was collected by filtration to obtain 74 mg of 2-(5-phenylpyridine-3-carboxamido)-4-(pyridin-2-yl)benzoic acid as a white 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 (0.19 mL) were added to the obtained solid
  5. stirringby stirring at room temperature for 1 hour
  6. additionA 10% aqueous solution of citric acid and ethyl acetate were added to the reaction mixture
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-3d6107b5b71f4462bbb6fc08bcb7f6ba
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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