3-(Trifluoromethyl)benzaldehyde → HCID 66590654, compound
Reaction equation
F[C:2](F)(F)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=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(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)CCCC[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]([CH2:34][CH2:35][CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([CH3:2])[CH:4]=3)[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Procedure
The title compound was prepared by substituting 3-m-tolylpropanal 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=7.1, 13.5, 1H), 7.65 (dd, J=4.8, 7.0, 2H), 7.34 (t, J=7.5, 2H), 7.29-7.22 (m, 2H), 7.12 (d, J=5.9, 1H), 7.09 (d, J=7.1, 1H), 7.06-7.02 (m, 1H), 4.42-4.31 (m, 1H), 3.24 (d, J=10.4, 1H), 2.97 (d, J=6.8, 0.5H), 2.71-2.58 (m, 4H), 2.56-2.44 (m, 1H), 2.43-2.38 (m, 0.5H), 2.35 (t, J=6.6, 3H), 2.29 (s, 1.5H), 2.27 (s, 1.5H), 2.27-2.23 (m, 1H), 2.17-2.11 (m, 1.5H), 1.89 (dt, J=6.1, 11.8, 1H), 1.79 (dd, J=7.4, 14.7, 1.5H), 1.72 (dt, J=7.6, 15.1, 1H), 1.66 (dd, J=5.9, 13.1, 0.5H), 1.42 (dt, J=7.5, 12.0, 1H), 1.37-1.30 (m, 0.5H), 1.23 (dd, J=6.5, 11.7, 3H), 0.71 (dd, J=3.0, 6.6, 3H); MS (ESI+) m/z 419 (M+H)+.
Sources & evidence
- ORD record
- ord-2303457c78ce4b298b74df3bde27e430
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129417B2
Reaction notes
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