Methanol → HCID 59843057, compound

Participants

Reaction Steps

To a solution of tert-butyl (3-(1-(2-(6-(1,2-dihydroxyethyl)-7-methoxyquinolin-4-yloxy)ethyl)-6-oxo-1,6-dihydropyridazin-3-yl)phenyl)methylcarbamate (30 mg, 53 μmol) in DMSO (0.5 mL)-THF (1 mL)-MeOH (1 mL) was added a solution of NaIO4 (80 mg, 374 μmol) in H2O (0.5 mL). After 5 h, the mixture was diluted with aqueous Na2SO3 (2 mL) and CH2Cl2 (5 mL). The organic layer was separated, the aqueous was extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried over MgSO4, concentrated, and purified on silica (1-6% MeOH in CH2Cl2) to give the product as a film (24 mg). LCMS (ESI pos. ion): calc'd for C29H30N4O6: 530.1; found 531.3 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H), 4.02 (s, 3 H), 4.36 (d, J=5.52 Hz, 2 H), 4.70 (t, J=5.52 Hz, 2 H), 4.81 (t, J=5.27 Hz, 2 H), 5.38 (none, 1H), 5.38 (m, 1 H), 6.73 (d, J=5.02 Hz, 1 H), 7.04 (d, J=9.54 Hz, 1 H), 7.35-7.47 (m, 3 H), 7.60 (d, J=7.53 Hz, 1 H), 7.65-7.73 (m, 2 H), 8.60 (s, 1 H), 8.72 (d, J=5.02 Hz, 1 H), 10.36 (s, 1 H).

Provenance & Evidence