Water → HCID 57891924, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-6-methyl indan-1-yl)acetate (23.0 mg, 0.053 mmol, from Step H) in THF (2 mL) and H2O (0.7 mL) lithium hydroxide monohydrate (4.0 mg, 0.107 mmol) was added. The reaction mixture was heated to 50° C. for 3 hr, cooled to ambient temperature and partitioned between EtOAc and 5% citric acid. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the residue by flash chromatography (2% CH3OH/CH2Cl2/0.2% HCO2H) on SiO2 afforded 28.0 mg of the title compound as a white film: 1H NMR (500 MHz, DMSO-d6) δ 1.34 (d, 6H, J=5.9 Hz), 1.60-1.74 (m, 1H), 2.25-2.39 (m, 2H), 2.55 (s, 3H), 2.64-2.92 (m, 3H), 3.42-3.47 (m, 1H), 4.85-5.05 (m, 1H), 7.32 (s, 1H), 7.56 (d, 1H, J=9.4 Hz), 7.86 (s, 1H), 8.38 (d, 1H, J=9.6 Hz), 8.51 (s, 1H); HPLC A: rt=3.84 min, m/z=418.5 (M+H)+.

Provenance & Evidence