Cispentacin → HCID 59604153, compound

HRID 219605Notes

Reaction equation

HRID 219605 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.[NH2:32][C@H:33]1[CH2:37][CH2:36][CH2:35][C@H:34]1[C:38]([OH:40])=[O:39]>>[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:32][C@@H:33]4[CH2:37][CH2:36][CH2:35][C@@H:34]4[C:38]([OH:40])=[O:39])=[CH:30][CH:31]=3)[N:20]=2)[N:10]=[N:9]1

Participants

3

Reactant 2

HCID 73305CispentacinHCID 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 59604153HCID 59604153, 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 (1R,2S)-2-aminocyclopentanecarboxylic acid (125 mg; 0.97 mmol), to give Example 177 as a white solid. 1H NMR: (TFA-d, 400 MHz) δ 10.08 (2H, d, J=6.0 Hz), 9.40 (2H, d, J=5.9 Hz), 9.18 (2H, d, J=7.9 Hz), 8.87 (1H, t, J=7.5 Hz), 8.79-8.66 (3H, m), 8.55 (1H, t, J=7.9 Hz), 8.28 (1H, t, J=9.3 Hz), 5.62 (1H, d, J=13.2 Hz), 5.48 (1H, d, J=13.3 Hz), 5.01-4.88 (1H, m), 4.49-4.37 (1H, m), 3.46-3.37 (1H, m), 3.36-3.25 (2H, m), 3.20-3.00 (2H, m), 2.97-2.89 (1H, m). LC/MS (Method C): 524 (M+H)+. HPLC (Method I) Rt 13.12 min (Purity: 96.4%).

Workup

  1. customobtained

Sources & evidence

ORD record
ord-d8466f97306c47b49278d26ba5d94117
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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