Lithium hydroxide, monohydrate → HCID 178476858, compound

Participants

Reaction Steps

A solution of Ethyl trans-4-(5-{[2-({4-[(diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-3-methyl-4-oxo-1,4-dihydroquinolin-8-yl)cyclohexanecarboxylate (Example 304, 72.0 mg, 0.097 mmol) in THF (0.125 mL) and MeOH (0.129 mL) was charged with a solution of lithium hydroxide, monohydrate (20.2 mg, 0.48 mmol) in H2O (0.129 mL) and allowed to stir at rt for 30 hrs. The reaction was concentrated under reduced pressure. The material was purified on an Isco combi-flash unit using DCM/MeOH (100:0→95:5) as eluent to afford 45 mg (60%) of the desired product. 1H NMR (400 MHz, MeOD) δ ppm 1.24-1.33 (m, 6 H) 1.66-1.86 (m, 4 H) 1.96-2.04 (m, 2 H) 2.12-2.14 (m, 3 H) 2.15-2.22 (m, 2 H) 3.39-3.43 (m, 1 H) 3.46-3.50 (m, 1 H) 3.91-3.94 (m, 3 H) 4.05-4.11 (m, 4 H) 6.88-6.94 (m, 1 H) 7.03-7.07 (m, 1 H) 7.47-7.52 (m, 1 H) 7.83-7.86 (m, 1 H) 8.01-8.06 (m, 1 H) 8.33-8.35 (m, 1 H) 8.50-8.59 (m, 1 H). MS (ES+): m/z 718.22/719.26 (100/98) [MH+]. HPLC: tR=1.43 min (Micromass TOF: polar—3 min).

Provenance & Evidence