1-Phenylcyclopentanecarboxylic acid → N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}cyclohexanecarboxamide

HRID 2363506Notes

Reaction equation

HRID 2363506 reaction equation
C1(C2(C(O)=[O:13])CCCC2)C=CC=CC=1.[F:15][C:16]([F:34])([F:33])[C:17]1[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=1)[CH2:20][N:21]1[CH2:25][C@H:24]2[C@@H:26]([NH2:29])[CH2:27][CH2:28][C@H:23]2[CH2:22]1.[CH2:35](N1C[C@H]2C(N)CC[C@H]2C1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[F:34][C:16]([F:33])([F:15])[C:17]1[CH:18]=[C:19]([CH:30]=[CH:31][CH:32]=1)[CH2:20][N:21]1[CH2:25][C@H:24]2[C@@H:26]([NH:29][C:35]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)=[O:13])[CH2:27][CH2:28][C@H:23]2[CH2:22]1

Participants

4

Reactant 3

HCID 661671-Phenylcyclopentanecarboxylic acidHCID 66590379(3aS*,4S*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 68411161(3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 68413881N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}cyclohexanecarboxamide

Procedure

The title compound was prepared by substituting cyclohexanecarboxylic acid for 1-phenylcyclopentanecarboxylic acid and (3aS*,4S*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 122 Step E for (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described for Example 1: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.74 (d, J=6.1, 1H), 7.71 (s, 1H), 7.62 (d, J=7.7, 1H), 7.57 (d, J=9.2, 1H), 7.47 (t, J=7.7, 1H), 4.48-4.41 (m, 1H), 3.53 (d, J=13.2, 1H), 3.47 (d, J=13.2, 1H), 2.84 (ddd, J=2.8, 7.9, 10.3, 1H), 2.75 (dd, J=2.8, 9.5, 1H), 2.51-2.43 (m, 1H), 2.37 (dd, J=2.8, 9.1, 1H), 2.34-2.29 (m, 1H), 2.27-2.19 (m, 2H), 1.94-1.83 (m, 2H), 1.80 (d, J=12.9, 1H), 1.73-1.60 (m, 6H), 1.57-1.51 (m, 1H), 1.35-1.27 (m, 1H), 1.22-1.10 (m, 3H); MS (ESI+) m/z 395 (M+H)+.

Sources & evidence

ORD record
ord-a5e58c3f65ad43cfaacaba09898e644c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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