3-(Trifluoromethyl)benzaldehyde → HCID 46213622, compound

HRID 1092518Notes

Reaction equation

HRID 1092518 reaction equation
F[C:2](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]([CH:52]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[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>>[C:52]1([CH:40]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:41][CH2:2][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:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

4

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 462130532,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamideHCID 665906853-Methyl-N-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-yl]-2-phenylbutanamide

Product 1

HCID 46213622HCID 46213622, compound

Procedure

The title compound was prepared by substituting 3,3-diphenylpropanal 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 8.59 (dd, J=2.9, 7.0, 1H), 7.65 (d, J=8.1, 2H), 7.46 (d, J=7.2, 1H), 7.44-7.37 (m, 4H), 7.33 (tt, J=3.7, 7.7, 6H), 7.28-7.24 (m, 1H), 7.23-7.18 (m, 1H), 4.44-4.34 (m, 1H), 4.28 (d, J=7.2, 1H), 4.20 (dd, J=5.4, 9.1, 1H), 3.24 (d, J=10.4, 1H), 2.93 (dd, J=2.4, 9.0, 0.5H), 2.71-2.61 (m, 1H), 2.56 (dd, J=2.7, 9.2, 0.5H), 2.54-2.50 (m, 0.5H), 2.50-2.43 (m, 0.5H), 2.43-2.36 (m, 0.5H), 2.35-2.28 (m, 3H), 2.24 (tt, J=5.1, 10.0, 2H), 2.18-2.07 (m, 2H), 1.94-1.83 (m, 1H), 1.82-1.74 (m, 0.5H), 1.68 (td, J=7.0, 14.3, 0.5H), 1.47-1.37 (m, 1H), 1.37-1.29 (m, 0.5H), 1.22 (dd, J=4.6, 6.4, 3H), 0.71 (dd, J=1.7, 6.7, 3H); MS (ESI+) m/z 481 (M+H)+.

Sources & evidence

ORD record
ord-c10e85b257fd43cc9a7b2e36bd4c9dd2
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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