Adipic Acid → HCID 178461898, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-{(1S)-1-[5-chloro-8-(3-fluorophenyl)cinnolin-7-yl]ethyl}-9H-purin-6-amine (10 g, 24 mmol) and hexanedioic acid (7.0 g, 48 mmol) in isopropyl alcohol (240 mL) was heated at 69° C. for 30 min which gave a milky solution. The reaction mixture was treated with heptane (120 mL) and heated for an additional 30 minUTES which gave a clear solution. The solution was cooled to 30° C. slowly and then to room temperature. The solid that precipitated was collected by filtration, rinsed with heptane (100 mL), and dried on the filter under vacuum for 2 d to give the desired product (12 g, 91%) as an off-white solid. LCMS for C21H16ClFN7 (M+H)+: m/z=420.1; Found: 420.3; 1H NMR (500 MHz, DMSO-d6): δ 12.9 (br s, 1H), 12.0 (br s, 2H), 9.47 (d, J=6.0 Hz, 1H), 8.49-8.43 (m, 1H), 8.41-8.31 (m, 1H), 8.25 (d, J=6.0 Hz, 1H), 8.14-8.05 (m, 2H), 7.68-7.55 (m, 2H), 7.37-7.23 (m, 2H), 5.46-5.34 (m, 1H), 2.22-2.17 (m, 4H), 1.52-1.47 (m, 7H).

Provenance & Evidence