Triethylamine → 4-tert-butyl-N-(3-(methylsulfonyl)phenyl)-2-(6-(trifluoromethyl)pyridin-2-yloxy)benzamide
Reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[CH3:57][S:58]([C:61]1[CH:62]=[C:63]([CH:65]=[CH:66][CH:67]=1)[NH2:64])(=[O:60])=[O:59]>CN(C=O)C>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:64][C:63]2[CH:65]=[CH:66][CH:67]=[C:61]([S:58]([CH3:57])(=[O:60])=[O:59])[CH:62]=2)=[O:10])=[C:7]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[N:16]=2)[CH:6]=1)([CH3:3])([CH3:4])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-tert-butyl-2-(6-(trifluoromethyl)pyridin-2-yloxy)benzoic acid (17 mg, 50 μmol), HATU (19 mg, 50 μmol), and triethylamine (20 μL, 0.15 mmol) in DMF (0.5 mL) was stirred for five minutes, then 3-(methylsulfonyl)aniline hydrochloride (11 mg, 55 μmol) was added. The reaction was stirred at room temperature for 20 hours and was purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to give 4-tert-butyl-N-(3-(methylsulfonyl)phenyl)-2-(6-(trifluoromethyl)pyridin-2-yloxy)benzamide. LC/MS: m/z 493.3 (M+H)+ at 1.97 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Workup
- customwas purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))
Sources & evidence
- ORD record
- ord-0a477ad639df4d27adb7c5c695795533
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779197B2
Reaction notes
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