Potassium Phosphate, Tribasic → HCID 118195282, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 117.1, 100 mg, 0.228 mmol), oxazolidin-2-one (79 mg, 0.913 mmol), copper iodide (4.35 mg, 0.023 mmol) and finely ground K3PO4 (143 mg, 0.672 mmol) were added to a MW vial. The vial was sealed, evacuated/purged with argon and a solution of trans-N,N′-dimethylcyclohexane-1,2-diamine (7.20 μL, 0.046 mmol) in dioxane (456 μL) was added. The RM was then stirred at 110° C. for 20 hr. The RM was diluted with EtOAc (5 mL), washed with 1M HCl (20 mL) and extracted with EtOAc. The combined extracts were sequentially washed with NH4OH (32%)/NH4Cl (sat.) 1:5 (10 mL), and brine (10 mL), dried over Na2SO4, and the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (RediSep® Silica gel column, 12 g, cyclohexane/EtOAc-EtOH+0.1% NH4OH (9:1), from 20% to 90% EtOAc-EtOH+0.1% NH4OH (9:1)). Second purification was performed by preparative HPLC (Condition 13, from 5% to 100% in 14 min) afforded the title compound as a brown solid. UPLC-MS (condition 1) tR=2.13 min, m/z=445.1 [M+H]+, m/z=443.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 4.03-4.21 (m, 2H) 4.32-4.49 (m, 2H) 7.39 (d, J=8.31 Hz, 2H) 7.72-7.83 (m, 1H) 7.84-7.93 (m, 2H) 8.06-8.17 (m, 2H) 8.96 (s, 2H) 9.22 (s, 1H) 10.49 (s, 1H).

Provenance & Evidence