(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → (2S,3aS,7aS)-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}octahydro-1H-indole-2-carboxamide

HRID 2363621Notes

Reaction equation

HRID 2363621 reaction equation
C(OC([N:8]([CH3:18])[C@@H:9]([CH2:13][C:14]([CH3:17])(C)C)[C:10]([OH:12])=O)=O)(C)(C)C.[F:19][C:20]([F:37])([F:36])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)=[N:25][CH:26]=1.F[C:39](F)(F)[C:40]1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=C[CH:41]=1>>[F:37][C:20]([F:19])([F:36])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH:35][C:10]([C@@H:9]4[CH2:13][C@H:14]5[C@H:18]([CH2:39][CH2:40][CH2:41][CH2:17]5)[NH:8]4)=[O:12])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)=[N:25][CH:26]=1

Participants

4

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590965(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 54672874(2S,3aS,7aS)-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}octahydro-1H-indole-2-carboxamide

Procedure

The title compound was prepared by substituting (2S,3aS,7aS)-1-(tert-butoxycarbonyl)octahydro-1H-indole-2-carboxylic acid for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Example 262 Step B for (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 587: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.66-8.59 (m, 1H), 8.32 (d, J=7.9, 1H), 7.67 (dd, J=8.9, 2.5, 1H), 6.36 (d, J=8.9, 1H), 4.38-4.29 (m, 1H), 3.94 (dd, J=10.6, 4.7, 1H), 3.72 (d, J=8.1, 1H), 3.58 (t, J=9.5, 2H), 3.33 (d, J=6.7, 1H), 3.23 (dd, J=9.4, 4.7, 1H), 3.18-2.94 (m, 1H), 2.80-2.68 (m, 1H), 2.66-2.57 (m, 1H), 2.27 (ddd, J=12.8, 10.6, 7.0, 1H), 2.15-2.05 (m, 1H), 1.96 (dddd, J=18.4, 16.6, 8.6, 4.9, 2H), 1.88-1.79 (m, 1H), 1.70-1.35 (m, 8H), 1.35-1.27 (m, 1H), 1.16 (tt, J=15.5, 6.5, 1H); MS (ESI+) m/z 423 (M+H)+.

Sources & evidence

ORD record
ord-e933a86156874bc59b71d911ef5be424
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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