Methylamine hydrochloride → 1-(4-{5-[1-(2-fluorophenyl)-5-pyridin-4-yl-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)-N-methylmethanamine

HRID 219580

Reaction equation

HRID 219580 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.Cl.[CH3:33][NH2:34]>>[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]([CH2:28][NH:34][CH3:33])=[CH:26][CH:25]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 6364545Methylamine hydrochlorideHCID 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 596040531-(4-{5-[1-(2-fluorophenyl)-5-pyridin-4-yl-1H-1,2,3-triazol-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)-N-methylmethanamine

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 methylamine hydrochloride (32.7 mg; 0.48 mmol) to give Example 129 as a white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.76-8.73 (2H, m), 7.97-7.87 (3H, m), 7.76-7.69 (1H, m), 7.64-7.49 (6H, m), 3.76 (2H, s), 2.31 (3H, s). LC/MS (Method C): 428 (M+H)+. HPLC (Method E) Rt 2.14 min (Purity: 98.9%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-91001d836a9c421aacd8e38217ffca38
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Linked notes

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