2-Bromo-4-(trifluoromethyl)pyridine → HCID 66997543, compound

HRID 2363648Notes

Reaction equation

F[C@@H:2]1[CH2:6][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.Cl[C:26]1[CH:31]=[CH:30][N: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][N:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=3)[CH2:22]2)[CH2:18][CH2:17]1)=[O:24])[CH2:3][CH:2]([CH3:6])[CH3:37]

Participants

Reactant 3

HCID 27815432-Bromo-4-(trifluoromethyl)pyridine

HCID 152943694-Chloro-2-(trifluoromethyl)pyrimidine

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

Product 1

HCID 66997543HCID 66997543, compound

Procedure

The title compound was prepared by substituting tert-butyl methyl((S)-4-methyl-1-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylamino)-1-oxopentan-2-yl)carbamate from Example 619 Step 1 for (2S,4S)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate and 4-chloro-2-(trifluoromethyl)pyrimidine for 2-bromo-4-(trifluoromethyl)pyridine in the procedure described in Example 637: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.23 (d, J=6.1, 1H), 7.73 (dd, J=6.7, 4.2, 1H), 6.34 (d, J=6.1, 1H), 4.25 (dt, J=14.3, 7.2, 1H), 3.73-3.52 (m, 3H), 3.28 (dd, J=11.2, 4.0, 1H), 3.15 (dd, J=7.9, 5.8, 1H), 2.83-2.65 (m, 2H), 2.39 (d, J=0.5, 3H), 2.13 (td, J=12.5, 7.3, 1H), 2.01-1.90 (m, 1H), 1.93-1.67 (br m, 1H), 1.85 (td, J=13.4, 6.6, 1H), 1.74-1.60 (m, 2H), 1.52 (ddd, J=14.0, 7.9, 6.3, 1H), 1.41 (td, J=13.3, 7.9, 1H), 0.93 (d, J=6.6, 3H), 0.89 (d, J=6.6, 3H); MS (ESI+) m/z 400 (M+H)+.

Sources & evidence

ORD record: ord-1652749d813249fe94863858c503e9a3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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