3-(Trifluoromethyl)benzaldehyde → HCID 46213111, compound
Reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=C(C=C[CH:10]=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]([CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)[CH2:39]CCCC1>>[C:3]([C:55]1[CH:54]=[CH:53][C:52]([CH2:40][CH2:34][CH2:39][N:24]2[CH2:25][C@@H:26]3[C@@H:19]([NH:18][C:16](=[O:17])[CH:15]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:14]([CH3:33])[CH3:13])[CH2:20][CH2:21][C@@H:22]3[CH2:23]2)=[CH:57][CH:56]=1)([CH3:4])([CH3:10])[CH3:2]Participants
Procedure
The title compound was prepared by substituting 3-(4-tert-butylphenyl)propanal 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 (t, J=8.5, 1H), 7.65 (t, J=6.6, 2H), 7.40 (dd, J=5.4, 8.0, 2H), 7.34 (t, J=7.4, 2H), 7.30-7.23 (m, 3H), 4.37 (dt, J=6.1, 11.1, 1H), 3.23 (d, J=10.4, 1H), 2.96 (dd, J=1.9, 8.9, 0.5H), 2.67 (ddd, J=6.7, 11.6, 23.3, 2H), 2.59 (dd, J=2.6, 9.3, 0.5H), 2.57-2.51 (m, 0.5H), 2.50-2.44 (m, 0.5H), 2.43-2.38 (m, 0.5H), 2.35 (t, J=8.1, 2H), 2.29 (dd, J=2.6, 8.8, 0.5H), 2.25 (t, J=7.1, 1H), 2.19 (d, J=7.2, 0.5H), 2.17-2.11 (m, 1H), 1.92-1.85 (m, 1H), 1.81 (dt, J=7.7, 15.5, 1H), 1.74 (dt, J=7.9, 15.9, 1H), 1.69-1.63 (m, 0.5H), 1.46-1.31 (m, 2H), 1.28 (s, 9H), 1.23 (dd, J=6.5, 13.4, 3H), 0.94-0.84 (m, 2H), 0.71 (dd, J=3.2, 6.6, 3H); MS (ESI+) m/z 461 (M+H)+.
Sources & evidence
- ORD record
- ord-1d9691e3ea2542e0a39da0fe746fe805
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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