(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66996890, compound

HRID 2363653Notes

Reaction equation

C(O[C:6]([N:8](C)[C@@H:9]([CH2:13]C(C)(C)C)[C:10](O)=[O:11])=O)(C)(C)C.[F:19][C:20]([F:37])([F:36])[C:21]1[CH:26]=[CH:25][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)=[CH:23][CH:22]=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][CH:25]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:11])[CH3:13]

Participants

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

HCID 66996860HCID 66996860, compound

HCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66996890HCID 66996890, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-alanine for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-[4-(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-4-amine from Example 607 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 8.16 (d, J=7.4, 1H), 7.57 (d, J=8.6, 2H), 6.62 (d, J=8.7, 2H), 4.36 (dd, J=13.0, 6.9, 1H), 3.53 (dd, J=10.2, 3.4, 1H), 3.39-3.33 (m, 1H), 3.29 (q, J=6.9, 1H), 3.22 (dd, J=9.7, 8.1, 1H), 3.01 (dd, J=9.9, 4.0, 1H), 2.77-2.63 (m, 2H), 2.42 (s, 3H), 2.20-2.13 (bs, 1H), 2.12-2.03 (m, 1H), 1.99-1.86 (m, 1H), 1.64 (dq, J=12.7, 7.9, 1H), 1.41 (d, J=6.8, 3H), 1.39-1.32 (m, 1H); MS (ESI+) m/z 356 (M+H)+.

Sources & evidence

ORD record: ord-9fab7a9164e346a5b3ab7beae1cd880c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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