HCID 68302560, compound → HCID 52938418, compound

Participants

Reaction Conditions

Reaction Steps

Prepared using General Procedure 11. To a stirred solution of (R)-tert-butyl (5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)(2-hydroxyethyl)carbamate INT-23 (15 mg, 0.03 mmol) in dioxane (1 mL) was added 4N HCl/dioxanes (116 μL, 0.116 mmol). After heating at 50° C. for 18 h, the mixture was concentrated and the resulting solid was purified by preparative HPLC to provide 9.53 mg (79%) of (R)-5-(3-(5-((2-hydroxyethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxy benzonitrile 50. LCMS-ESI (m/z) calculated for C24H26N4O3: 418.5; found 419.2 [M+H]+, tR=2.52 min. 1H NMR (400 MHz, CDCl3) δ 8.39 (d, J=2.2 Hz, 1H), 8.32 (dd, J=8.9, 2.2 Hz, 1H), 8.04 (d, J=7.7 Hz, 1H), 7.60 (d, J=7.6 Hz, 1H), 7.39 (t, J=7.7 Hz, 1H), 7.12 (d, J=9.1 Hz, 1H), 4.88-4.70 (m, 1H), 4.54 (s, 1H), 3.78 (d, J=12.1 Hz, 2H), 3.62 (s, 2H), 3.24 (dt, J=18.0, 5.6 Hz, 1H), 3.18-2.89 (m, 3H), 2.16 (d, J=5.2 Hz, 2H), 2.10-1.75 (m, 2H), 1.47 (d, J=6.1 Hz, 6H).

Provenance & Evidence