Potassium Iodide → HCID 46864321, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-methoxy-4-(3-methylisoxazol-5-yl)phenyl)-1H-1,2,4-triazol-3-amine (580 mg, 1.234 mmol), potassium carbonate (682 mg, 4.94 mmol), and potassium iodide (410 mg, 2.468 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/mM, 30-85% B, 25 min) to afford 9-(4-fluorophenyl)-N-(3-methoxy-4-(3-methylisoxazol-5-yl)phenyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[1,5-a]azepin-2-amine (145 mg, 0.301 mmol, 24% yield). LC-MS (M+H)+ 434.3. 1H NMR (400 MHz, methanol-d4) δ ppm 7.67 (d, J=8.56 Hz, 1 H) 7.49 (d, J=2.01 Hz, 1 H) 7.23 (dd, J=8.56, 5.29 Hz, 2H) 7.09 (t, J=8.69 Hz, 2 H) 6.99 (dd, J=8.56, 2.01 Hz, 1 H) 4.35-4.44 (m, 1H) 4.15-4.35 (m, 2 H) 3.87 (s, 3 H) 2.30 (s, 3 H) 2.19-2.28 (m, 1 H) 2.00-2.10 (m, 1 H) 1.72-1.94 (m, 4 H).

Provenance & Evidence