Piperidin-4-ol → HCID 59604111, compound

HRID 219589Notes

Reaction equation

HRID 219589 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.[OH:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][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][N:36]4[CH2:37][CH2:38][CH:33]([OH:32])[CH2:34][CH2:35]4)=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 79341Piperidin-4-olHCID 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 59604111HCID 59604111, 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, (100 mg; 0.24 mmol) and 4-hydroxypiperidine (49.1 mg; 0.48 mmol) to give Example 141 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), 7.61 (2H, dd, J=4.5, 1.6 Hz), 7.52 (4H, t, J=8.4 Hz), 4.57 (1H, d, J=4.1 Hz), 3.56-3.43 (3H, m), 2.70 (2H, d, J=10.5 Hz), 2.13-2.04 (2H, m), 1.74 (2H, d, J=12.0 Hz), 1.48-1.37 (2H, m). LC/MS (Method C): 498 (M+H)+. HPLC (Method E) Rt 2.13 min (Purity: 99.9%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-aef6cc0c97de409c9d0c27d3a8c51892
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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