(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

HRID 2363619Notes

Reaction equation

HRID 2363619 reaction equation
C(OC([N:8]([CH3:18])[C@@H:9]([CH2:13][C:14]([CH3:17])([CH3:16])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.FC(F)(F)C1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=CC=1>>[CH3:18][NH:8][C@H:9]([C:10]([NH:35][C@@H:32]1[C@@H:30]2[C@@H:29]([CH2:28][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:37])([F:36])[F:19])=[CH:26][N:25]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:17]

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 66997494N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-leucine 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 (s, 1H), 8.37 (d, J=7.5, 1H), 7.68 (dd, J=8.9, 2.5, 1H), 6.40 (d, J=8.9, 1H), 4.49-4.38 (m, 1H), 3.83 (d, J=10.7, 1H), 3.68 (dd, J=11.0, 7.3, 1H), 3.63-3.52 (m, 1H), 3.33 (d, J=8.2, 1H), 3.27 (dd, J=8.3, 5.9, 1H), 2.77 (h, J=8.8, 2H), 2.45 (s, 3H), 2.17 (dt, J=12.4, 7.1, 1H), 2.14-1.98 (m, 1H), 2.02-1.86 (m, 2H), 1.79-1.67 (m, 2H), 1.66-1.55 (m, 1H), 1.48-1.36 (m, 1H), 0.94 (d, J=6.6, 3H), 0.88 (d, J=6.6, 3H); MS (ESI+) m/z 399 (M+H)+.

Sources & evidence

ORD record
ord-c85bfefe242144bcb02f9bd369f79e92
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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