3-(Trifluoromethyl)benzaldehyde → HCID 66590215, compound

HRID 2363493Notes

Reaction equation

HRID 2363493 reaction equation
[F:1]C(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]CCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1>>[F:1][C:36]1[CH:35]=[C:34]([CH2:40][CH2:52][CH2:57][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:39]=[CH:38][CH:37]=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 66590215HCID 66590215, compound

Procedure

The title compound was prepared by substituting 3-(3-fluorophenyl)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 (400 MHz, pyridine-d5) δ ppm 8.52 (s, 1H), 7.69-7.61 (m, 2H), 7.33 (t, J=7.5, 2H), 7.27 (ddd, J=3.5, 7.6, 10.6, 2H), 7.14-6.95 (m, 3H), 4.43-4.29 (m, 1H), 3.23 (d, J=10.4, 1H), 2.97 (dd, J=2.2, 8.8, 0.5H), 2.72-2.58 (m, 3H), 2.57-2.44 (m, 1H), 2.44-2.38 (m, 0.5H), 2.36-2.26 (m, 3H), 2.25-2.16 (m, 1H), 2.16-2.09 (m, 1H), 1.93-1.83 (m, 1H), 1.77 (dt, J=7.2, 14.6, 1.5H), 1.72-1.63 (m, 1.5H), 1.47-1.27 (m, 2H), 1.22 (dd, J=6.5, 10.4, 3H), 0.94-0.83 (m, 1H), 0.71 (dd, J=2.7, 6.7, 3H); MS (ESI+) m/z 423 (M+H)+.

Sources & evidence

ORD record
ord-1a6e3b073cd8444f83adcc966dd96c5a
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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