Potassium Iodide → HCID 46864320, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-1,2,4-triazol-3-amine (559 mg, 1.188 mmol), potassium carbonate (657 mg, 4.75 mmol), and potassium iodide (394 mg, 2.376 mmol) in DMF (8 mL) was heated at 55° C. for 16 hrs. The solvent was removed in vacuo. The crude product was purified using reverse phase preparatory-HPLC(Column: Phenomenex Luna C18 30×100 mm, Solvent A=10 mM Ammonium Acetate in 95:5 water/ACN, Solvent B=10 mM Ammonium Acetate in 5:95 water/ACN, Flow rate: 40 ml/min, 30-85% B, 25 min) to afford 9-(4-fluorophenyl)-N-(3-methoxy-4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (82 mg, 0.189 mmol, 16% yield). LC-MS (M+H)+ 435.3. 1H NMR (400 MHz, methanol-d4) δ ppm 7.83 (d, J=8.56 Hz, 1 H) 7.56 (d, J=2.01 Hz, 1 H) 7.19-7.28 (m, 2 H) 7.08 (t, J=8.81 Hz, 2 H) 6.99 (dd, J=8.56, 2.01 Hz, 1 H) 4.17-4.43 (m, 3 H) 3.85 (s, 3 H) 2.39 (s, 3 H) 2.17-2.31 (m, 1 H) 2.01-2.11 (m, 1 H) 1.78-1.98 (m, 4 H).

Provenance & Evidence