2-Bromo-5-(trifluoromethyl)pyridine → HCID 66997402, Verbindung

HRID 2363658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2363658
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][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][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][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=3)[CH2:22]2)[CH2:18][CH2:17]1)=[O:24])[CH:3]([CH3:2])[CH3:37]

Komponenten

4

Edukt 3

HCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 27815432-Bromo-4-(trifluoromethyl)pyridineHCID 66997253(2S,4S)-tert-butyl 4-fluoro-2-((3aR,4S,6aS)-octahydrocyclopenta[c]pyrrol-4-ylcarbamoyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 66997402HCID 66997402, Verbindung

Versuchsvorschrift

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-5-(trifluoromethyl)pyridine for 2-bromo-4-(trifluoromethyl)pyridine in the procedure described in Example 637: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.63 (dd, J=1.6, 0.8, 1H), 8.31 (d, J=7.5, 1H), 7.67 (dt, J=19.9, 10.0, 1H), 6.40 (d, J=8.9, 1H), 4.50-4.37 (m, 1H), 3.83 (d, J=10.4, 1H), 3.72-3.63 (m, 1H), 3.61-3.51 (m, 1H), 3.33 (d, J=8.4, 1H), 2.94 (d, J=5.8, 1H), 2.81-2.67 (m, 2H), 2.43 (s, 3H), 2.23-1.87 (m, 4H), 1.69 (dq, J=12.7, 8.2, 1H), 1.41 (dtd, J=13.2, 8.0, 5.0, 1H), 1.08 (dd, J=6.9, 2.1, 6H); MS (ESI+) m/z 385 (M+H)+.

Quellen und Nachweise

ORD-Eintrag
ord-8d10905a5b2b445d906dbf7883cbc7ac
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691865B2

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