Trifluoroacetic acid → HCID 57879360, compound

HRID 1673548Notes

Reaction equation

HRID 1673548 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22]C(C)(C)C)=[O:21])=[C:18]([NH:29][C:30]([C:32]2[CH:33]=[N:34][C:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:36][CH:37]=2)=[O:31])[CH:17]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH2:8]([C:16]1[CH:28]=[CH:27][C:19]([C:20]([OH:22])=[O:21])=[C:18]([NH:29][C:30]([C:32]2[CH:33]=[N:34][C:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:36][CH:37]=2)=[O:31])[CH:17]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67343254HCID 67343254, compound

Product 1

HCID 57879360HCID 57879360, compoundYield 43.2%

Procedure

1.7 mL of trifluoroacetic acid was added to 0.17 g of tert-butyl 4-phenethyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoate and stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and hexane and diisopropyl ether were added to the obtained residue and a solid substance was separated by filtration. Ethyl acetate and water were added to the obtained solid substance and pH was adjusted to pH 6.8 with a saturated sodium hydrogen carbonate aqueous solution. A solid substance was separated by filtration to obtain 65 mg of 4-phenethyl-2-(6-(piperidin-1-yl)pyridine-3-carboxamido)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and hexane and diisopropyl ether
  2. additionwere added to the obtained residue
  3. customa solid substance was separated by filtration
  4. additionEthyl acetate and water were added to the obtained solid substance and pH
  5. customA solid substance was separated by filtration

Sources & evidence

ORD record
ord-7c86d342531247adbfd164a6cb5e6246
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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