Trifluoroacetic acid → HCID 136198185, compound

HRID 454589Notes

Reaction equation

HRID 454589 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:43])=[C:19]([CH:42]=2)[C:20]([NH:22][C:23]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27]C(C)(C)C)=[O:26])=[O:21])[CH:12]=[CH:11][CH:10]=1>>[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([OH:43])=[C:19]([CH:42]=2)[C:20]([NH:22][C:23]2[CH:35]=[C:34]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:33]=[CH:32][C:24]=2[C:25]([OH:27])=[O:26])=[O:21])[CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136198175HCID 136198175, compound

Product 1

HCID 136198185HCID 136198185, compoundYield 63.7%

Procedure

Trifluoroacetic acid (5 mL) was added to the obtained tert-butyl 2-(5-(6-aminopyridin-2-yl)-2-hydroxybenzamido)-4-phenylbenzoate (0.032 g), followed by stirring at room temperature for 12 hours. The solvent was evaporated under reduced pressure, and water and ethyl acetate were added thereto. After adjusting the pH to 6 with a saturated aqueous solution of sodium bicarbonate, the solid substance was collected by filtration. Carbon dioxide gas was introduced into a solution mixture of water (1 mL), methanol (0.5 mL), and dioxane (0.5 mL) containing the obtained solid substance, and the solid substance was collected by filtration to obtain 0.018 g of 2-(5-(6-aminopyridin-2-yl)-2-hydroxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and ethyl acetate
  2. additionwere added
  3. filtrationthe solid substance was collected by filtration
  4. additionCarbon dioxide gas was introduced into a solution mixture of water (1 mL), methanol (0.5 mL), and dioxane (0.5 mL)
  5. additioncontaining the obtained solid substance
  6. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-e962c2170a1b4b858b16c630dfe2a0c4
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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