Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=3)[N:20]=2)[N:10]=[N:9]1.[NH:32]1[CH2:37][CH2:36][CH2:35][CH:34]([C:38]([OH:40])=[O:39])[CH2:33]1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:25]=[CH:26][C:27]([CH2:28][N:32]4[CH2:37][CH2:36][CH2:35][CH:34]([C:38]([OH:40])=[O:39])[CH2:33]4)=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1Participants
Procedure
The title compound was prepared following the procedure described for Example 94, but starting from 4-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl) benzaldehyde, obtained as described in Example 113, Step 1, (200 mg; 0.48 mmol) and piperidine-3-carboxylic acid (125 mg; 0.97 mmol) to give Example 158 as a yellow solid. 1H NMR: (DMSO-d6, 400 MHz) δ 12.25 (1H, br s), 8.75 (2H, dd, J=4.5, 1.6 Hz), 7.97-7.88 (3H, m), 7.76-7.69 (1H, m), 7.61 (2H, dd, J=4.5, 1.7 Hz), 7.57-7.47 (4H, m), 3.59 (2H, t, J=14.7 Hz), 2.85 (1H, d, J=11.0 Hz), 2.68 (1H, d, J=11.2 Hz), 2.50-2.42 (1H, m), 2.28-1.95 (2H, m), 1.84 (1H, d, J=12.1 Hz), 1.68 (1H, dd, J=12.2, 4.7 Hz), 1.58-1.31 (2H, m). LC/MS (Method C): 526 (M+H)+. HPLC (Method F) Rt 2.83 min (Purity: 98.7%).
Workup
- customobtained
Sources & evidence
- ORD record
- ord-6ac46829a31f403c81ad50ec9acd05ad
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202856B2
Linked notes
Loading…