Diisopropylethylamine → HCID 69621153, compound

Participants

Reaction Steps

(R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 27, 0.050 g, 0.08 mmol) was taken up in THF (2 mL) and 2-morpholinoacetaldehyde 2,2,2-trifluoroacetate (0.024 g, 0.10 mmol) and DIEA (0.043 mL, 0.24 mmol) were added. The mixture was stirred at RT for 15 min. then sodium triacetoxyborohydride (0.078 g, 0.37 mmol) was added and reaction was stirred at RT for 6 hrs. The reaction was then quenched with NaHCO3 and extracted with DCM three times. Organics were combined and dried over Na2SO4 then the solvent was removed in vacuo. The residue was purified by flash column chromatography on silica gel using (dichloromethane-methanol) to give (R)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.026 mg, 44%).

Provenance & Evidence