3-(Trifluoromethyl)benzaldehyde → HCID 54673857, compound
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][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(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)CCCCC1>>[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][C:8]3[CH:9]=[CH:10][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:4][CH:5]=3)[CH2:25]2)[CH2:21][CH2:20]1)=[O:17]Participants
Procedure
The title compound was prepared by substituting 4-(trifluoromethyl)benzaldehyde 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 8.62 (t, J=7.8, 1H), 7.64 (dd, J=7.0, 11.8, 4H), 7.51 (d, J=8.0, 1H), 7.46 (d, J=7.9, 1H), 7.33 (dd, J=7.4, 12.1, 2H), 7.29-7.24 (m, 1H), 4.40-4.30 (m, 1H), 3.58 (d, J=13.7, 0.5H), 3.48 (t, J=13.8, 1H), 3.35 (d, J=13.7, 0.5H), 3.23 (dd, J=1.4, 10.4, 1H), 2.92 (dd, J=2.7, 9.0, 0.5H), 2.69-2.60 (m, 1H), 2.57 (dd, J=2.7, 9.1, 1H), 2.54-2.47 (m, 0.5H), 2.47-2.39 (m, 1H), 2.39-2.32 (m, 0.5H), 2.31-2.20 (m, 2H), 2.19-2.11 (m, 1H), 1.95-1.82 (m, J=6.4, 37.0, 1H), 1.77 (dt, J=6.4, 13.8, 0.5H), 1.69 (dt, J=6.9, 19.1, 0.5H), 1.50-1.25 (m, J=34.6, 62.0, 1.5H), 1.21 (t, J=6.4, 3H), 0.70 (d, J=5.1, 3H); MS (ESI+) m/z 445 (M+H)+.
Sources & evidence
- ORD record
- ord-fe7397f6b9014af58ee5bb9ee783d779
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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