Water → 2-(3-(4-(2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)-1-methyl-1H-pyrazol-5-yl)piperidin-1-yl)-2-methylpropan-1-ol

Participants

Reaction Steps

To a solution of ethyl 2-methyl-2-[3-(1-methyl-4-{4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-5-yl)piperidin-1-yl]propanoate (35 mg, 0.060 mmol) in dry THF (2 ml), was added LiAlH4 (11.4 mg, 0.300 mmol) in small portions at room temperature. The resulting mixture was heated to reflux for 1 h. Water (1 mL) was added to quench the reaction. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to afford 248 (10 mg, 31% yield). LCMS (ESI): RT=4.72 min, m/z: 545.4 [M+H+]. 1H NMR (500 MHz, DMSO-d6) δ 8.39 (d, J=8.5 Hz, 1H), 7.91 (s, 1H), 7.43 (s, 1H), 7.09-7.08 (m, 1H), 6.93 (d, J=1.5 Hz, 1H), 5.86-5.83 (m, 1H), 4.53 (d, J=6.0 Hz, 4H), 4.27-4.25 (m, 1H), 3.89 (s, 3H), 3.28-3.25 (m, 2H), 2.99-2.96 (m, 3H), 2.44-2.40 (m, 2H), 2.26 (s, 3H), 2.08-2.06 (m, 1H), 1.58-1.70 (m, 3H), 1.47-1.45 (m, 6H), 0.93-0.91 (m, 6H)

Provenance & Evidence