Hydrochloric Acid → HCID 68466412, compound

Participants

Reaction Conditions

Reaction Steps

Add K2CO3 (1.1 equiv., 13.2 mg, 0.095 mmol) to bisazaindole iodide 18 (52 mg, 0.0862 mmol) in CH3CN (6.0 mL) at 60° C., then add 1-methylpiperazine (1.10 equiv., 9.515 mg, 10.55 μL, 0.095 mmol). After stirring for 2 h at 60° C., add extra K2CO3 (13.2 mg) and 1-methylpiperazine (21 μL) and continue stirring at 60° C. for 30 h. The reaction mixture is then concentrated to give a residue, which is treated with 2N HCl and washed with CH2Cl2. The aqueous phase is then treated with 2N NaOH until pH>10 and extracted with CH2Cl2, dried (MgSO4) and concentrated under vacuum, to give 21 (10 mg, 20.2%) as an ivory-colored solid: 1H NMR (CDCl3) δ 8.35 (dd, 1H, J=4.4, 1.1 Hz), 7.72 (dd, 1H, J=4.4, 1.1 Hz), 7.67 (d, 2H, J=8.4 Hz), 7.60 (s, 1H), 7.15 (m, 2H), 7.03 (d, 2H, J=8.4 Hz), 6.98 (s, 1H), 5.28 (s, 3H), 4.26 (t, 2H), 4.00 (s, 3H), 3.97 (s, 3H), 2.86 (t, 2H), 2.55 (m broad, 8H), 2.30 (s, 3H). TLC (MeOH at 10%/CH2Cl2, 0.25% of NH3) Rf=0.35, m/z obs.=575 (M+1).

Provenance & Evidence