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0 °C

To a solution of 3-{4-[2-(benzyloxy)-5-chloropyridin-3-yl]-2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-6-yl}-1,2,4-oxadiazol-5(4H)-one (23 mg, 0.03 mmol) in anhydrous CH2Cl2 at 0° C., Et3SiH (0.029 mL, 0.18 mmol) and PdCl2 (2 mg, 0.01 mmol) were added. The reaction was stirred at 0° C. for 0.5 hour and then concentrated. The residue was purified on a C-18 column eluting with 40% water/60% acetonitrile to afford 5-chloro-3-{2-[(4aR,7aR)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl}pyridin-2(1H)-one. 1H NMR (400 MHz, CD3OD) δ 8.09 (s, 1H), 8.04 (br s, 1H), 7.76 (d, J=2.8 Hz, 1H), 4.01 (m, 1H), 3.83-3.93 (m, 3H), 3.62 (m, 1H), 3.54 (m, 1H), 3.38 (m, 1H), 3.12 (m, 1H), 2.96 (m, 1H), 2.28 (m, 1H), 1.97 (m, 1H), 1.49-1.82 (m, 6H), 1.19-1.25 (m, 2H), 0.91-1.00 (m, 2H), 0.78 (d, J=6.4 Hz, 3H), 0.57-0.74 (m, 3H). MS ES calc'd. for C28H32ClN7O4 [M+H]+ 566. found 566.

1. concentrationconcentrated
2. customThe residue was purified on a C-18 column
3. washeluting with 40% water/60% acetonitrile