4-Aminopyridine → HCID 178520577, compound

Participants

Reaction Steps

Add N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.189 g; 1.0 equiv; 0.71 mmoles) to a solution containing 5-(4H-1,2,4-triazol-3-yl)pentanoic acid (0.40 g 1.0 equiv; 0.71 mmoles), followed by dimethylformamide (2 mL). Stir the resulting solution at room temperature until homogeneous. Add 4-pyridinamine, N,N-dimethyl-(0.017 g; 0.2 equiv; 0.141 mmoles), and cool the solution to 0° C. Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.204 g; 1.5 equiv; 1.06 mmoles) in one portion. Allow the mixture to warm to room temperature and stir for 30 minutes. Add dichloromethane (2 mL), heat to 40° C., and stir for 24 hours. Dilute with 250 mL water and then 50 mL ethyl acetate. Extract the mixture with ethyl acetate (5×25 mL). Wash the combined organic extracts with brine (10 mL). Dry the organics over magnesium sulfate, filter, concentrate, and purify via column chromatography (hexanes to 12% methanol in ethyl acetate) to give 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-5-(4H-1,2,4-triazol-3-yl)pentan-1-one (0.08 g; 27% yield) as a white foam: MS (m/z): 418 (M+1).

Provenance & Evidence