2-Bromo-4-(trifluoromethyl)pyridine → HCID 66997214, compound

HRID 2363659Notes

Reaction equation

HRID 2363659 reaction equation
F[C@@H:2]1C[N:5]([C:7](OC(C)(C)C)=O)[C@H:4]([C:14](=[O:24])[NH:15][C@@H:16]2[C@@H:23]3[C@@H:19]([CH2:20][NH:21][CH2:22]3)[CH2:18][CH2:17]2)[CH2:3]1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=1.Br[C:37]1C=C(C(F)(F)F)C=CN=1>>[CH3:7][NH:5][C@H:4]([C:14]([NH:15][C@@H:16]1[C@@H:23]2[C@@H:19]([CH2:20][N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=3)[CH2:22]2)[CH2:18][CH2:17]1)=[O:24])[CH:3]([CH3:2])[CH3:37]

Participants

4

Reactant 3

HCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 66997253(2S,4S)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66997214HCID 66997214, compound

Procedure

The title compound was prepared by substituting tert-butyl methyl{(2S)-3-methyl-1-[(3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylamino]-1-oxobutan-2-yl}carbamate from Example 733 for (2S,4S)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate and 2-bromo-6-(trifluoromethyl)pyridine for 2-bromo-4-(trifluoromethyl)pyridine in the procedure described in Example 637: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.28 (d, J=7.4, 1H), 7.53-7.46 (m, 1H), 6.98 (t, J=6.4, 1H), 6.52 (d, J=8.6, 1H), 4.47-4.36 (m, 1H), 3.72 (dd, J=10.9, 2.9, 1H), 3.65-3.58 (m, 1H), 3.53 (dd, J=10.8, 8.0, 1H), 3.29 (dd, J=11.0, 3.6, 1H), 2.93 (d, J=5.8, 1H), 2.73 (t, J=5.7, 2H), 2.42 (s, 3H), 2.18-2.09 (m, 2H), 1.97-1.88 (m, 1H), 1.67 (dq, J=12.8, 8.0, 1H), 1.38 (dtd, J=12.9, 7.9, 4.9, 1H), 1.07 (dd, J=6.8, 2.2, 6H); MS (ESI+) m/z 385 (M+H)+.

Sources & evidence

ORD record
ord-fc4ed524ae5143c9833daf89e3459d26
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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