Potassium Hydroxide → HCID 178463583, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of {1-[3-phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]ethyl}-(9H-purin-6-yl)amine from Example 21 (200 mg, 0.393 mmol) and 2M KOH (0.8 mL) in MeOH (4 mL) was stirred at 70° C. for 72 h. Volatiles were removed under reduced pressure and the resulting residue was diluted with water. The pH of the solution was adjusted to 1 by addition of 1M HCl and then to 8 by addition of a saturated solution of NaHCO3. The aqueous layer was extracted with EtOAc (×3) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by preparative HPLC (Phenomenex Gemini 5 μm C18 on a gradient 10-98% 0.1% HCO2H in acetonitrile/water) and then by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) affording 116 as a white solid (83 mg, 60%). LCMS: RT 3.98 min [M+H]+ 355.0. 1H NMR (DMSO, 400 MHz): δ 11.29 (1H, s), 8.21-8.09 (2H, m), 7.71-7.55 (3H, m), 7.52-7.42 (5H, m), 7.32 (1H, t, J=7.39 Hz), 7.13 (1H, t, J=7.93 Hz), 7.02 (1H, t, J=7.93 Hz), 5.96 (1H, s), 1.62 (3H, d, J=6.93 Hz)

Provenance & Evidence