Diisopropylethylamine → HCID 178516973, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 1-(trans-4-aminocyclohexyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.1050 g, 0.339 mmol), 2-chloro-1,5-naphthyridine (0.067 g, 0.407 mmol, 00358), and diisopropylethylamine (0.177 ml, 1.017 mmol, Sigma-Aldrich Chemical Company, Inc.) in DMSO (0.484 ml) and heated to 120° C. for 2 days. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, 100×50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 90% over 15 min. Fractions containing product were collected and concentrated. The product was taken up in DCM and loaded onto a Silicycle Si-carbonate cartridge and washed with DCM and MeOH to remove any salts to give the title compound (6.4 mg, 0.016 mmol, 4.7% yield). LCMS showed product peak at 1.434 min (m+1=402.0). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.09-1.24 (m, 4 H) 1.37-1.53 (m, 2 H) 1.94 (d, J=11.93 Hz, 2 H) 2.39 (d, J=12.13 Hz, 2 H) 2.68 (qd, J=12.91, 3.13 Hz, 2 H) 2.97-3.09 (m, 1 H) 4.08-4.24 (m, 1 H) 4.47 (tt, J=12.32, 3.91 Hz, 1 H) 6.85 (d, J=9.19 Hz, 1 H) 7.45 (dd, J=8.41, 4.30 Hz, 1 H) 7.91-7.96 (m, 2 H) 7.97 (d, J=8.61 Hz, 1 H) 8.03 (d, J=9.19 Hz, 1 H) 8.60 (d, J=3.33 Hz, 1 H)

Provenance & Evidence