3-(Trifluoromethyl)benzaldehyde → HCID 46213557, compound

HRID 2363482Notes

Reaction equation

HRID 2363482 reaction equation
FC(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].C1(C(C2CCCCC2)[C:41](N[C@@H]2[C@H]3[C@H](CNC3)CC2)=[O:42])CCCCC1>>[CH3:41][O:42][C:10]1[CH:3]=[CH:4][C:5]([CH2:6][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:8][CH:9]=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 46213557HCID 46213557, compound

Procedure

The title compound was prepared by substituting 4-methoxybenzaldehyde 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=8.3, 10.9, 1H), 7.63 (dd, J=2.8, 7.4, 2H), 7.39-7.28 (m, 4H), 7.28-7.23 (m, 1H), 6.98 (dd, J=8.7, 10.2, 2H), 4.41-4.30 (m, 1H), 3.68 (s, 3H), 3.57 (d, J=12.9, 0.5H), 3.48 (d, J=12.9, 0.5H), 3.42 (d, J=12.9, 0.5H), 3.31 (d, J=12.8, 0.5H), 3.21 (d, J=10.4, 1H), 2.90 (dd, J=2.8, 8.9, 0.5H), 2.69-2.59 (m, 1H), 2.56 (dd, J=2.9, 9.0, 1H), 2.53-2.46 (m, 1H), 2.45-2.33 (m, 1H), 2.32-2.26 (m, J=10.0, 1H), 2.24 (t, J=5.2, 1H), 2.15 (dt, J=6.3, 12.3, 0.5H), 1.96-1.88 (m, 0.5H), 1.88-1.79 (m, 0.5H), 1.79-1.65 (m, 1H), 1.48-1.24 (m, J=19.9, 48.8, 3H), 1.20 (dd, J=4.3, 6.4, 3H), 0.70 (dd, J=2.0, 6.7, 2H); MS (ESI+) m/z 407 (M+H)+.

Sources & evidence

ORD record
ord-62e69b24b30b4e71bed65220351a1b2b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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