tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate → 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acid

HRID 1673498Notes

Reaction equation

HRID 1673498 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([O:13]C(C)(C)C)=[O:12])=[C:9]([NH:20][C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([N:29]4[CH:33]=[CH:32][CH:31]=[CH:30]4)[CH:28]=3)=[O:22])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[C:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([OH:13])=[O:12])=[C:9]([NH:20][C:21]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([N:29]4[CH:33]=[CH:32][CH:31]=[CH:30]4)[CH:28]=3)=[O:22])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 67342180tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate

Product 1

HCID 578794974-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

10 mL of trifluoroacetic acid was added to the obtained tert-butyl 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoate and stirred an room temperature for 2 hours. The solvent was evaporated under reduced pressure, ethyl acetate and water were added and pH was adjusted to pH 7.0 with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue and a solid substance was separated by filtration to obtain 23 mg of 4-phenyl-2-(5-(1H-pyrrol-1-yl)pyridine-3-carboxamido)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, ethyl acetate and water
  2. additionwere added
  3. customThe organic layer was separated
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether was added to the obtained residue
  6. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-064a19b31007467db7307ac17675c872
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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