Trifluoroacetic acid → 4-(4-(Methylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid
Reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15](C)[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([O:28]C(C)(C)C)=[O:27])=[C:24]([NH:35][C:36]([C:38]3[CH:39]=[N:40][CH:41]=[C:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:43]=3)=[O:37])[CH:23]=2)=[CH:18][CH:17]=1)=O)(C)(C)C>>[CH3:13][NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:34]=[CH:33][C:25]([C:26]([OH:28])=[O:27])=[C:24]([NH:35][C:36]([C:38]3[CH:39]=[N:40][CH:41]=[C:42]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:43]=3)=[O:37])[CH:23]=2)=[CH:20][CH:21]=1Participants
3
Procedure
Trifluoroacetic acid (4.0 mL) was added to the obtained tert-butyl 4-(4-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (0.16 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, and ethanol and water were added to the obtained solid substance. After adjusting the pH to 5.5 with a 1 mol/L aqueous solution of sodium hydroxide, the solid substance was collected by filtration to obtain 0.11 g of 4-(4-(methylamino)phenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a light yellow solid.
Workup
- customThe solvent was evaporated under reduced pressure, and diisopropyl ether
- additionwas added to the obtained residue
- filtrationThe solid substance was collected by filtration, and ethanol and water
- additionwere added to the obtained solid substance
- filtrationthe solid substance was collected by filtration
Sources & evidence
- ORD record
- ord-f4e66986f0cc4e5ca35d973085555d80
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492582B2
Reaction notes
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