Toluene → HCID 118006077, compound

Participants

Reaction Steps

{2,4-Dichloro-3-[4-(1H-pyrazol-1-yl)benzyl]quinolin-6-yl}(1-methyl-1H-imidazol-5-yl)pyrimidin-2-ylmethanol (58 mg, 0.107 mmol, Example 130), toluene (2 mL), and sodium methoxide (116 mg, 2.14 mmol) were combined in a round bottom flask equipped with a stirbar and condenser under an N2 atmosphere. The reaction contents were heated to reflux and refluxed overnight. The reaction was cooled to room temperature and the contents were transferred to a separatory funnel with EtOAc dilution, and extracted with saturated, aqueous NH4Cl then saturated, aqueous NaHCO3 solutions. The organic phase was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude material was purified via reverse phase chromatography using acetonitrile with 0.05% trifluoroacetic acid in water as eluent. The fractions from the purification containing the desired product were transferred to a separatory funnel with EtOAc and extracted with a saturated, aqueous NaHCO3 solution. The aqueous layer was separated, extracted with EtOAc, then the combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound. MS (ESI): mass calcd. for C29H24ClN7O2, 537.2. m/z found, 538.3 [M+H]+. 1H NMR (400 MHz, CD3OD) δ ppm 8.84 (d, J=4.9 Hz, 2H), 8.39 (d, J=1.8 Hz, 1H), 8.13-8.07 (m, 1H), 7.86 (dd, J=8.8, 2.0 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.66 (d, J=1.3 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 7.42 (t, J=4.9 Hz, 1H), 7.32 (d, J=8.6 Hz, 2H), 6.50-6.45 (m, 1H), 6.42 (s, 1H), 4.27 (s, 2H), 4.04 (s, 3H), 3.39 (s, 3H).

Provenance & Evidence