(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-norvalinamide

HRID 2363618Notes

Reaction equation

HRID 2363618 reaction equation
C(O[C:6]([N:8](C)[C@@H:9]([CH2:13][C:14](C)(C)[CH3:15])[C:10](O)=[O:11])=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>>[CH3:6][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:19])([F:36])[F:37])=[CH:26][N:25]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:11])[CH2:13][CH2:14][CH3:15]

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 66996850N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-norvalinamide

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norvaline 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 8.67-8.57 (m, 1H), 8.30 (d, J=7.4, 1H), 7.68 (dd, J=8.9, 2.4, 1H), 6.40 (d, J=8.9, 1H), 4.48-4.37 (m, 1H), 3.87-3.78 (m, 1H), 3.67 (dd, J=11.1, 7.4, 1H), 3.59 (dd, J=10.7, 8.1, 1H), 3.37-3.29 (m, 1H), 3.20 (dd, J=6.9, 6.2, 1H), 2.82-2.67 (m, 2H), 2.43 (s, 3H), 2.16 (dtd, J=12.4, 7.2, 4.9, 1H), 2.00-1.90 (m, 1H), 1.83 (ddt, J=12.8, 9.5, 6.3, 1H), 1.76-1.64 (m, 2H), 1.60-1.35 (m, 4H), 0.86 (t, J=7.3, 3H); MS (ESI+) m/z 385 (M+H)+.

Sources & evidence

ORD record
ord-dbfc578b78d1497b9d621c85f16373e6
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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