Aminoisobutyric acid → N-(4-{5-[1-(2-fluorophenyl)-5-pyridin-4-yl-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-2-methylalanine

HRID 219604Notes

Reaction equation

HRID 219604 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:33]([CH3:38])([CH3:37])[C:34]([OH:36])=[O:35]>>[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:33]([CH3:38])([C:34]([OH:36])=[O:35])[CH3:37])=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 6119Aminoisobutyric acidHCID 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 59604115N-(4-{5-[1-(2-fluorophenyl)-5-pyridin-4-yl-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-2-methylalanine

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 2-amino-2-methylpropanoic acid (100 mg; 0.97 mmol), to give Example 174 as a white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.76-8.73 (2H, m), 8.00 (2H, d, J=8.1 Hz), 7.94-7.87 (1H, m), 7.77-7.60 (5H, m), 7.55-7.47 (2H, m), 3.96 (2H, s), 1.36 (6H, s). LC/MS (Method C): 498 (M+H)+. HPLC (Method E) Rt 2.35 min (Purity: 98.9%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-43125fb387d545dc82b4f61eb0c518f9
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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