Hydrochloric Acid → 6-Chloro-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaen-16-one Hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzamide (80.0 mg, 0.206 mmol) in 2-methoxyethanol (1.1 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (154 μL). The resulting mixture was heated at 150° C. in a microwave for 15 min. The cloudy mixture was filtered. The crude cake was recrystallized from MeOH to give the desired product as an off-white powder (25 mg, 34%). LCMS for C18H14ClN5O (M+H)+: m/z=352.0. 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1H), 9.50 (t, J=2.0 Hz, 1H), 9.05 (t, J=2.0 Hz, 1H), 8.24 (m, 1H), 7.86 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.28 (m, 2H), 7.10 (t, J=7.6 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H).

Provenance & Evidence