3-(Trifluoromethyl)benzaldehyde → HCID 46213242, compound

HRID 2363524Notes

Reaction equation

HRID 2363524 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH2:13]1[C@@H:17]2[CH2:18][CH2:19][C@@H:20]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)(=[O:24])=[O:23])[C@@H:16]2[CH2:15][NH:14]1.C1(C(C2CCCCC2)C(N[C@@H]2[C@H]3[C@H](CNC3)CC2)=O)CCCCC1>>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:2]([F:12])([F:11])[F:1])[CH:10]=1)[CH2:6][N:14]1[CH2:15][C@H:16]2[C@H:20]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=3)(=[O:24])=[O:23])[CH2:19][CH2:18][C@H:17]2[CH2:13]1

Participants

4

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 462130532,2-Dicyclohexyl-N-((3aS,4S,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)acetamideHCID 66590947HCID 66590947, compound

Product 1

HCID 46213242HCID 46213242, compound

Procedure

The title compound was prepared by substituting 3,5-bis(trifluoromethyl)benzaldehyde for 3-(trifluoromethyl)benzaldehyde and N-((3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)-3-(trifluoromethyl)benzenesulfonamide from Example 191 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 9.53 (d, J=7.4, 1H), 8.42 (s, 1H), 8.30 (d, J=7.9, 1H), 8.03 (s, 1H), 7.96 (s, 2H), 7.81 (d, J=7.8, 1H), 7.60 (t, J=7.9, 1H), 3.82-3.74 (m, 1H), 3.59 (s, 2H), 2.68-2.64 (m, 1H), 2.59-2.49 (m, 2H), 2.38-2.33 (m, 1H), 2.23 (dt, J=5.9, 8.9, 2H), 1.97-1.81 (m, 2H), 1.59 (ddd, J=8.2, 11.8, 13.0, 1H), 1.35-1.24 (m, 1H); MS (ESI+) m/z 561 (M+H)+.

Sources & evidence

ORD record
ord-46936d85a8f142ef9435ed25159d82e4
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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