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

HRID 2363622Notes

Reaction equation

HRID 2363622 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:14]5[C:18](=[CH:39][CH:40]=[CH:41][CH: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 54672875(2S)-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}indoline-2-carboxamide

Procedure

The title compound was prepared by substituting (S)-1-(tert-butoxycarbonyl)indoline-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 (400 MHz, pyridine-d5) δ ppm 8.63 (dd, J=1.6, 0.8, 1H), 8.21 (d, J=7.6, 1H), 7.67 (dd, J=9.0, 2.5, 1H), 7.19-7.07 (m, 2H), 6.83 (dd, J=11.7, 4.3, 2H), 6.54-6.46 (m, 1H), 6.35 (d, J=8.9, 1H), 4.69 (td, J=10.8, 3.5, 1H), 4.46-4.30 (m, 1H), 3.82-3.71 (m, 1H), 3.65-3.48 (m, 3H), 3.42-3.24 (m, 2H), 2.80-2.62 (m, 2H), 2.19-2.03 (m, 1H), 1.97-1.80 (m, 1H), 1.62 (dq, J=12.8, 8.2, 1H), 1.45-1.28 (m, 1H); MS (ESI+) m/z 417 (M+H)+.

Sources & evidence

ORD record
ord-cebfa5642a7c445ea83ff7b4e611ccfc
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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