Lithium hydroxide, monohydrate → HCID 178476857, compound

Participants

Reaction Steps

A solution of ethyl cis-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 305, 61.7 mg, 0.083 mmol) in THF (0.11 mL) and MeOH (0.11 mL) was charged with a solution of lithium hydroxide, monohydrate (17.4 mg, 0.41 mmol) in H2O (0.11 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 22.3 mg (38%) of the desired product. 1H NMR (400 MHz, MeOD) δ ppm 1.24-1.30 (m, 6H) 1.76-1.89 (m, 6H) 2.11-2.15 (m, 3H) 2.34 (d, J=4.80 Hz, 2H) 2.73 (br. s., 1H) 2.99 (s, 1H) 3.29 (br. s., 1H) 3.34 (s, 1H) 3.89-3.94 (m, 3H) 4.02-4.13 (m, 4H) 6.87 (dt, J=8.21, 2.34 Hz, 1H) 7.03 (t, J=2.02 Hz, 1H) 7.41 (d, J=8.59 Hz, 1H) 7.84 (d, J=0.76 Hz, 1H) 8.03 (d, J=8.34 Hz, 1H) 8.33 (s, 1H) 8.49 (d, J=6.32 Hz, 1H). MS (ES+): m/z 718.15/719.19 (100/98) [MH+]. HPLC: tR=1.47 min (Micromass TOF: polar—3 min).

Provenance & Evidence