Dichloromethane → HCID 131731428, compound

Participants

Reaction Steps

tert-butyl 6-{5-[4-(2-methylpiperidin-1-yl)-3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}-3,4-dihydroisoquinoline-2(1H)-carboxylate obtained from step 1 was dissolved in DCM (3 mL) and TFA (1 mL). The resulting solution was stirred at RT for 1 hour and the solvent was evaporated in vacuo to give a light yellow oil. The latter was filtered through a short plug of alumina (c-hexane/EtOAc, 80/20 then 50/50) to give a light yellow oil that was triturated in a Et2O/HCl (1 M) mixture (1:1, 2 mL), filtered and washed with Et2O to the title compound as an off-white solid. 1H NMR (DMSO-d6) δ 9.30 (bs, 2H), 8.45-8.41 (m, 1H), 8.38 (m, 1H), 8.01-7.98 (m, 2H), 7.86 (d, J=8.5 Hz, 1H), 7.46 (d, J=8.0 Hz, 1H), 4.41 (m, 2H), 3.54-3.42 (m, 3H), 3.18-3.08 (m, 3H), 2.97-2.93 (m, 1H), 2.65-2.59 (m, 1H), 1.80-1.77 (m, 2H), 1.63-1.30 (m, 4H), 0.78 (d, J=6 Hz, 3H). HPLC (Method A) Rt 4.61 min (Purity: 100.0%). LC/MS (method B): 443.2 (M+H)+.

Provenance & Evidence