3-(Trifluoromethyl)benzaldehyde → HCID 46213113, compound
Reaction equation
FC(F)(F)C1C=C(C=CC=1)C=O.[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][NH:24][CH2:25]2)[CH2:21][CH2:20]1)=[O:17].[CH:34]1([CH:40](C2CCCCC2)[C:41](N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH3:13][CH:14]([CH3:33])[CH:15]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:16]([NH:18][C@@H:19]1[C@@H:26]2[C@@H:22]([CH2:23][N:24]([CH2:41][CH2:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Procedure
The title compound was prepared by substituting 2-phenylacetaldehyde for 3-(trifluoromethyl)benzaldehyde and 3-methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide from Example 83 Step A for 2,2-dicyclohexyl-N-[(3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]acetamide in the procedure described for Example 54: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.57 (dd, J=5.2, 12.0, 1H), 7.65 (t, J=7.1, 2H), 7.38-7.23 (m, 8H), 4.40-4.29 (m, 1H), 3.23 (d, J=10.5, 1H), 3.00 (dd, J=2.6, 9.0, 0.5H), 2.80 (t, J=7.8, 1H), 2.75-2.70 (m, 1H), 2.70-2.61 (m, 1H), 2.61-2.52 (m, 1H), 2.52-2.46 (m, 1H), 2.43 (dd, J=7.6, 8.7, 0.5H), 2.38 (dd, J=2.7, 8.8, 1H), 2.34 (dd, J=2.7, 8.5, 1H), 2.26 (d, J=8.3, 0.5H), 2.24-2.18 (m, 1H), 2.12 (td, J=6.4, 12.4, 0.5H), 1.91-1.82 (m, 1H), 1.76 (dt, J=6.2, 18.7, 0.5H), 1.70-1.61 (m, 0.5H), 1.46-1.26 (m, 2H), 1.23 (dd, J=6.5, 13.5, 3H), 0.97-0.83 (m, 1H), 0.71 (dd, J=2.7, 6.7, 3H); MS (ESI+) m/z 391 (M+H)+.
Sources & evidence
- ORD record
- ord-fd469f70e4334ca0b327f1715b598f19
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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