Trifluoroacetic acid → 3-morpholino-6-(2-((tetrahydro-2H-pyran-4-yl)methyl)phenyl)quinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

(2-(2-Amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol (0.085 g, 0.203 mmol, see Example 12) was dissolved in DCM (20 mL) and treated with triethylsilane (1.0 mL, 6.26 mmol) and TFA (2.0 mL, 26.9 mmol). The mixture was heated to 70° C. for 30 min after which analysis showed the reduction was complete. The solution was evaporated to dryness under reduced pressure. The crude was partitioned between water (10 mL), saturated sodium bicarbonate (10 mL) and DCM (20 mL). The organic layer was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (0-10% methanol in DCM gradient) gave the desired 3-morpholino-6-(2-((tetrahydro-2H-pyran-4-yl)methyl)phenyl)quinolin-2-amine. MS (ESI, pos. ion) m/z: 404 (M+1).

Provenance & Evidence