4,4-Difluoropiperidine → 4-{1-(2-fluorophenyl)-4-[3-(4-{[(3R)-3-fluoropyrrolidin-1-yl]methyl}phenyl)-1,2,4-oxadiazol-5-yl]-1H-1,2,3-triazol-5-yl}pyridine

HRID 219598Notes

Reaction equation

HRID 219598 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.F[C:33]1([F:39])[CH2:38][CH2:37][NH:36][CH2:35]C1>>[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][N:36]4[CH2:37][CH2:38][C@@H:33]([F:39])[CH2:35]4)=[CH:26][CH:25]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 27583524,4-DifluoropiperidineHCID 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 596040504-{1-(2-fluorophenyl)-4-[3-(4-{[(3R)-3-fluoropyrrolidin-1-yl]methyl}phenyl)-1,2,4-oxadiazol-5-yl]-1H-1,2,3-triazol-5-yl}pyridine

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 4,4-difluoropiperidine (168 mg; 0.97 mmol) to give Example 161 as a white solid. 1H NMR: (CDCl3, 400 MHz) δ 8.72 (2H, dd, J=4.5, 1.7 Hz), 8.05 (2H, d, J=8.1 Hz), 7.63-7.52 (2H, m), 7.45 (2H, d, J=8.0 Hz), 7.40-7.34 (3H, m), 7.22-7.15 (1H, m), 3.61 (2H, s), 2.57 (4H, t, J=5.4 Hz), 2.07-1.94 (4H, m). LC/MS (Method C): 518 (M+H)+. HPLC (Method I) Rt 15.55 min (Purity: 97.6%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-66c68bb78d9d49c99c70bd9ed75f4496
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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