Trifluoroacetic acid → 4-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acid

HRID 1673544Notes

Reaction equation

HRID 1673544 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[CH:42]=[CH:41][CH:40]=[CH: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>C(Cl)Cl>[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[CH:42]=[CH:41][CH:40]=[CH: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

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67342233tert-butyl 4-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate

Product 1

HCID 578793034-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 mL of trifluoroacetic acid was added to 1.0 mL of methylene chloride solution containing 20 mg of tert-butyl 4-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate and stirred at room temperature for 1 hour and 30 minutes. Tine solvent was evaporated under reduced pressure and diisopropyl ether was added to the obtained residue and a solid substance was separated by filtration to obtain 17 mg of 4-phenethyl-2-(6-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acid as white solid.

Workup

  1. customTine solvent was evaporated under reduced pressure and diisopropyl ether
  2. additionwas added to the obtained residue
  3. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-691cc2642012419e9c79df255c27f04f
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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