Trifluoroacetic acid → 4-(2-Methoxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid
Reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[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][CH:35]=[C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:37]=2)=[O:31])[CH:17]=1>>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[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][CH:35]=[C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:37]=2)=[O:31])[CH:17]=1Participants
3
Procedure
Trifluoroacetic acid (4.0 mL) was added to the obtained tert-butyl 4-(2-methoxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoate (61 mg), 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 dioxane (3.0 mL), water, and a 2 mol/L aqueous solution of sodium hydroxide (0.080 mL) were added to the obtained residue. After adjusting the pH to 7.6 with 1 mol/L hydrochloric acid, the solid substance was collected by filtration to obtain 32 mg of 4-(2-methoxyphenyl)-2-(5-phenylpyridine-3-carboxamido)benzoic acid as a white 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 dioxane (3.0 mL), water
- additiona 2 mol/L aqueous solution of sodium hydroxide (0.080 mL) were added to the obtained residue
- filtrationthe solid substance was collected by filtration
Sources & evidence
- ORD record
- ord-01c3ae02dccf4815bbb5c39fa1aa2e0d
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492582B2
Reaction notes
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