Reaction Steps
A mixture of 1-tert-butyl-6-(5-{4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-1-yl)-1λ3,3-oxazocan-2-one (105 mg, 0.250 mmol) and LiAlH4 (51 mg, 1.3 mmol) in THF (5 mL) was refluxed for 1 hr. MeOH was added to quench reaction and the solid was filtered off. The filtrate was evaporated to afford the crude product, which was purified by preparative HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give 267 (17 mg, 13% yield). LCMS (ESI): RT=4.80 min, m/z: 489.3 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.52 (d, J=8.5 Hz, 1H), 8.01 (s, 1H), 7.95 (s, 1H), 7.55 (d, J=1.5 Hz, 1H), 7.26-7.24 (m, 1H), 7.10 (d, J=1.5 Hz, 1H), 6.39 (d, J=1.5 Hz, 1H), 5.01-4.97 (m, 1H), 4.71-4.69 (m, 1H), 4.58 (t, J=13.5, 4H), 4.17-4.13 (m, 1H), 3.91-3.87 (m, 1H), 3.19 (s, 3H), 2.83 (d, J=12 Hz, 2H), 2.16-2.09 (m, 5H), 1.90 (t, J=53 Hz, 2H), 1.80 (d, J=11.5, 2H), 1.12 (d, J=6.5, 3H)
