Morpholine → {4-Chloro-2-morpholin-4-yl-3-[4-(1H-pyrazol-1-yl)benzyl]quinolin-6-yl}(1-methyl-1H-imidazol-5-yl)[6-(trifluoromethyl)pyridin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

{2,4-Dichloro-3-[4-(1H-pyrazol-1-yl)benzyl]quinolin-6-yl}(1-methyl-1H-imidazol-5-yl)pyrimidin-2-ylmethanol (100 mg, 0.164 mmol, Intermediate 65), morpholine (144 mg, 1.64 mmol) and DMF (2 mL) were combined in a reaction tube, then sealed and heated to 100° C. and maintained at that temperature for 48 hours. The vessel was then cooled to room temperature and the solvent was removed by a stream of nitrogen. The crude material was purified via reverse phase chromatography using acetonitrile with ammonium hydroxide in water as eluent to afford the title compound. MS (ESI): mass calcd. for C34H29ClF3N7O2, 659.2. m/z found, 660.3 [M+H]+. 1H NMR (600 MHz, CDCl3) δ ppm 8.80 (d, J=1.9 Hz, 1H), 8.17 (d, J=2.0 Hz, 1H), 7.88-7.83 (m, 3H), 7.63 (d, J=1.4 Hz, 1H), 7.60-7.52 (m, 3H), 7.25 (s, 1H), 7.22 (d, J=8.7 Hz, 2H), 7.10 (s, 1H), 6.42 (dd, J=2.4, 1.9 Hz, 1H), 6.21 (d, J=0.9 Hz, 1H), 4.38 (s, 2H), 3.83-3.75 (m, 4H), 3.30 (s, 3H), 3.25-3.16 (m, 4H).

Provenance & Evidence