Methanol → Acridine

Participants

Reaction Steps

To a solution of 76 mg (0.168 mmol) of TFP ester 4 in 3 mL of chloroform was added 94 μL of triethylamine (0.67 mmol). 1.23 ml of a 50 mg/mL solution of 9-(6-aminohexylamino)acridine dihydrochloride in methanol (61.5 mg, 0.168 mmol) was added to the stirred solution. HPLC analysis after 1 hour showed complete reaction of the starting TFP ester. The reaction mixture was partitioned between 15 mL of methylene chloride and 10 mL of water. The organic phase was washed with 10 mL of water, dried over sodium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel and the desired product was eluted with a gradient of 90:5:5-methylene chloride: triethylamine:methanol in hexanes. Removal of solvents gave the desired product 5 as a red solid: TLC (90:5:5-methylene chloride: triethylamine:methanol) Rf =0.79; 1H NMR (CDCl3) δ 8.12 (d, 2H, J=8.8 Hz,), 8.07 (d, 2H, J=8.8 Hz), 7.68 (t, 2H, J=6.9 Hz), 7.37 (t, 2H, J=7.4 Hz), 5.60 (s, 1H), 5.2 (br s, 1H), 3.82 (t, 2H, J=7.1 Hz), 3.21 (q, 2H, J=6.6 Hz), 2.54 (m, 2H), 2.2 (m, 10H), 1.98 (s, 3 H), 1.8-1.65 (m, 6H), 1.5-1.3 (m, 6H).

Provenance & Evidence