2-Methoxyethylamine → 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-methoxyethanamine

HRID 219577

Reaction equation

HRID 219577 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.[CH3:32][O:33][CH2:34][CH2:35][NH2:36]>>[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:36][CH2:35][CH2:34][O:33][CH3:32])=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 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 59604062N-(4-{5-[1-(2-fluorophenyl)-5-pyridin-4-yl-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)-2-methoxyethanamine

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, (100 mg; 0.24 mmol) and 2-methoxyethanamine (36.4 mg; 0.48 mmol) to give Example 114 as a white solid. 1H NMR: (CDCl3, 400 MHz) δ 8.73-8.69 (2H, m), 8.05 (2H, d, J=8.0 Hz), 7.66-7.52 (2H, m), 7.46 (2H, d, J=8.0 Hz), 7.40-7.33 (3H, m), 7.18 (1H, t, J=9.1 Hz), 3.88 (2H, s), 3.53 (2H, t, J=5.1 Hz), 3.36 (3H, s), 2.82 (2H, t, J=5.1 Hz). LC/MS (Method C): 472 (M+H)+. HPLC (Method F) Rt 3.07 min (Purity: 96.5%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-e4d86c6b3dc64e0eab3c2e6e638b5640
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Linked notes

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