L-Proline → HCID 59604086, compound

HRID 219596Notes

Reaction equation

HRID 219596 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.[NH:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]([OH:39])=[O:38]>>[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:32]4[CH2:36][CH2:35][CH2:34][C@H:33]4[C:37]([OH:39])=[O:38])=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 145742L-ProlineHCID 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 59604086HCID 59604086, 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, (200 mg; 0.48 mmol) and (S)-pyrrolidine-2-carboxylic acid (111 mg; 0.97 mmol) to give Example 159 as an off-white solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.77-8.74 (2H, m), 7.98-7.87 (3H, m), 7.76-7.69 (1H, m), 7.64-7.57 (4H, m), 7.52 (2H, t, J=8.5 Hz), 4.11 (1H, d, J=13.5 Hz), 3.72 (1H, d, J=13.5 Hz), 3.31 (1H, dd, J=8.9, 5.9 Hz), 3.04-2.96 (1H, m), 2.50 (1H, d, J=8.5 Hz), 2.16-2.07 (1H, m), 1.94-1.84 (1H, m), 1.84-1.73 (2H, m). LC/MS (Method C): 412 (M+H)+. HPLC (Method I) Rt 15.21 min (Purity: 95.3%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-73b3319e2ed8426b9c12f3dcc4e786d0
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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