Reaction Steps
tert-Butyl 2-(3-(3-(2-allyl-2H-tetrazol-5-yl)phenethoxy)-N-cyclohexylpropanamido)ethyl(2-(5-(tert-butoxycarbonyloxy)-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-8-yl)ethyl)carbamate [Example 15, Step v)] (170 mg), 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (97 mg) and tetrakis(triphenylphosphine)palladium(0) (24 mg, 0.02 mmol) were dissolved in DCM (2 mL) and sealed into a microwave tube. The reaction was heated to 100° C., over a period of 30 min in the microwave reactor. After cooling to rt, TFA (1 mL) was added and the mixture stirred for 30 min. The mixture was concentrate in vacuo do give a crude product. The crude product was purified by preparative HPLC on a Phenomenex Gemini column using a gradient of aqueous 0.1% trifluoroacetic acid in acetonitrile as eluent to afford the titled compound (41.8 mg) as a solid. MS [M+H]+=578.3 (calc=578.3091) (MultiMode+) 1H NMR (400 MHz, CD3OD) δ 7.92 (s, 1H), 7.80 (dt, J=1.6 and 7.4 Hz, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.44 (dt, J=1.5 and 7.9 Hz, 1H), 6.70 (d, J=8.5 Hz, 1H), 6.46 (d, J=8.2 Hz, 1H), 4.61 (s, 2H), 3.74 (t, J=6.5 Hz, 2H), 3.72 (t, J=6.0 Hz, 2H), 3.71-3.63 (m, 1H), 3.48 (t, J=5.8 Hz, 2H), 3.14 (t, J=7.1 Hz, 2H), 3.04 (t, J=5.7 Hz, 2H), 2.94 (t, J=6.3 Hz, 2H), 2.87 (t, J=7.0 Hz, 2H), 2.63 (t, J=6.0 Hz, 2H), 1.79-1.71 (m, 2H), 1.68-1.57 (m, 3H), 1.44-1.23 (m, 4H), 1.16-1.03 (m, 1H)
