Phenyl isocyanate → HCID 18332643, compound

Participants

Reaction Steps

To a suspension of 15 mg of 2-[(piperidin-3-yl)-methylamino]-4-[benzimidazol-1-yl]pyrimidine (from EXAMPLE 6) in 2 mL of THF was added 7.6 mg of phenyl isocyanate. The mixture was stirred at room temperature overnight. An additional 7.6 mg of phenyl isocyanate was added and the mixture was stirred for an additional 24 h, then concentrated. The residue was purified by flash chromatography, eluting with 1:1 hexanes-acetone, to yield 12 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H), 8.37 (d, J=5.3, 1H) 8.17 (d, J=7.3 Hz, 1H), 7.36-7.44 (m, 2H), 7.22-7.34 (m, 3H), 7.00 (t, J=7.3 Hz, 1H), 6.78 (d, J=5.3 Hz, 1H), 6.52 (s, 1H), 5.75 (br s, 1H), 3.97 (dd, J=3.4, 13.0 Hz, 1H), 3.77 (dt, J=4.4, 13.0 Hz, 1H), 3.41-3.57 (m, 2H), 3.14 (br t, J=10.5 Hz, 1H), 3.02 (dd, J=8.9, 13.3 Hz, 1H), 1.92-2.08(m, 2H), 1.72-1.84 (m, 1H), 1.53-1.64 (m, 1H), 1.41 (ddt, J=3.9, 9.8, 10.1 Hz, 1H). Mass spectrum (EST) 428.2 (M+1).

Provenance & Evidence