2-Bromo-4-(trifluoromethyl)pyridine → HCID 66997413, compound

HRID 2363649Notes

Reaction equation

HRID 2363649 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[N:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=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[N:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=3)[CH2:22]2)[CH2:18][CH2:17]1)=[O:24])[CH2:3][CH:2]([CH3:6])[CH3:37]

Participants

4

Reactant 3

HCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 282425263-Chloro-6-(trifluoromethyl)pyridazineHCID 66997253(2S,4S)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 66997413HCID 66997413, 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 3-chloro-6-(trifluoromethyl)pyridazine for 2-bromo-4-(trifluoromethyl)pyridine in the procedure described in Example 637: 1H NMR (400 MHz, pyridine-d5) δ ppm 7.76 (s, 1H), 7.46 (d, J=9.4, 1H), 6.66 (d, J=9.4, 1H), 4.34-4.25 (m, 1H), 3.82 (d, J=3.9, 2H), 3.75-3.64 (m, 2H), 3.44 (dd, J=11.3, 4.7, 1H), 3.16 (dd, J=7.9, 5.8, 1H), 2.88-2.68 (m, 2H), 2.40 (s, 3H), 2.20-2.09 (m, 1H), 1.98 (dtd, J=13.1, 8.0, 5.0, 1H), 1.91-1.80 (m, 1H), 1.74-1.62 (m, 2H), 1.48 (dddd, J=15.8, 13.4, 7.9, 6.0, 2H), 0.94 (d, J=6.6, 3H), 0.90 (d, J=6.6, 3H); MS (ESI+) m/z 400 (M+H)+.

Sources & evidence

ORD record
ord-df50a7b031d34faea2bac706fc2e43b7
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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