2-Bromo-5-(trifluoromethyl)pyridine → N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-valinamide

Participants

Reaction Steps

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)+.

Provenance & Evidence