49805-32-5 → HCID 59604148, compound

HRID 219603Notes

Reaction equation

HRID 219603 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.[NH2:32][C@H:33]1[CH2:37][CH2:36][C@@H:35]([C:38]([OH:40])=[O:39])[CH2:34]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][NH:32][C@@H:33]4[CH2:37][CH2:36][C@H:35]([C:38]([OH:40])=[O:39])[CH2:34]4)=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 150203549805-32-5HCID 866481594-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl) benzaldehyde

Product 1

HCID 59604148HCID 59604148, compound

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 (1R,3S)-3-aminocyclopentanecarboxylic acid (125 mg; 0.97 mmol), to give Example 169 as a white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.76-8.71 (2H, m), 7.98 (2H, d, J=8.0 Hz), 7.93-7.85 (1H, m), 7.76-7.68 (1H, m), 7.64-7.58 (4H, m), 7.53-7.46 (2H, m), 3.97 (1H, d, J=13.8 Hz), 3.89 (1H, d, J=13.8 Hz), 3.27 (1H, t, J=4.8 Hz), 2.76-2.67 (1H, m), 1.94-1.73 (6H, m). LC/MS (Method C): 524 (M+H)+. HPLC (Method F) Rt 2.86 min (Purity: 96.2%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-373a1c862ad941cf9f5e7f511e0ee6ea
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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