HCID 86722469, compound → HCID 86722468, compound

Participants

Reaction Steps

9-(4-Fluorophenyl)-12b-(pyridin-2-ylmethyl)-1,5,6,7,9,12b-hexahydrobenzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-3 (2H)-one (116, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (9.28 g, 21.16 mmol) in THF (170 mL) and pyridine (22 mL) with palladium on carbon (10%) (0.690 g, 0.648 mmol) was hydrogenated in a Parr shaker at 50 psi hydrogen and rt for about 8 h. The mixture was filtered through a pad of Celite® and the pad was washed with DCM. The filtrate was concentrated under reduced pressure and the material was purified on silica gel (330 g) using a gradient from 0-100% EtOAc in DCM. Product fractions were combined and concentrated under reduced pressure to yield rac-(4aR,12bR)-9-(4-fluorophenyl)-12b-(pyridin-2-ylmethyl)-1,4,4a,5,6,7,9,12b-octahydrobenzo[3,4]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-3(2H)-one (118, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (5.55 g, 59.5%); LC/MS, method 3, Rt=2.46 min, MS m/z 441 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.40-8.37 (m, 2H), 8.31-8.29 (m, 1H), 8.19 (s, 1H), 7.80 (s, 1H), 7.47-7.38 (m, 3H), 7.09-7.05 (m, 1H), 6.61 (d, J=7.8 Hz, 1H), 3.83 (d, J=12.9 Hz, 1H), 3.63-3.56 (m, 1H), 3.40-3.35 (m, 1H), 2.97 (d, J=13.0 Hz, 1H), 2.62-1.81 (m, 9H), 1.75-1.65 (m, 2H).

Provenance & Evidence