4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzoic acid → Methyl 3-fluoro-4-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzoate
Reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[F:13].[CH3:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][N:18]1[C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=O)=[CH:25][C:24]=1[C:32]([F:35])([F:34])[F:33]>>[F:13][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:3]=1[C:2]1[N:1]=[C:27]([C:26]2[CH:30]=[CH:31][C:23]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]3[CH3:16])=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=2)[O:15][N:14]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
3
Procedure
The title compound was prepared following procedure described for example 4, step 1, but starting from Intermediate 2 (106.09 mg; 0.50 mmol) and Intermediate 15 (143.64 mg; 0.50 mmol). The reaction mixture was filtered through a SPE NH2 column (2 g) and rinsed with ACN. The filtrate was passed through a SPE SCX column (2 g) and rinsed with ACN. After evaporation of the solvents, the crude product was suspended in ACN, filtrated and dried under vacuo, affording the title compound as a yellow solid. 1H NMR (DMSO-d6, 300 MHz) δ 8.45 (dd, J=8.5, 1.9 Hz, 1H), 8.38 (d, J=2.0 Hz, 1H), 8.34-8.29 (m, 1H), 8.01 (dd, J=8.1, 1.6 Hz, 1H), 7.94 (dd, J=10.9, 1.4 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 3.92 (s, 3H), 3.20-3.13 (m, 1H), 2.98-2.94 (m, 1H), 2.66-2.58 (m, 1H), 1.81-1.76 (m, 2H), 1.63-1.27 (m, 4H), 0.79 (d, J=6.0 Hz, 3H). HPLC (Method A) Rt 6.60 min (Purity: 70.1%).