Aluminium lithium hydride → 2-(3-(5-(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)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropan-1-ol

Participants

Reaction Steps

To a solution of ethyl 2-(3-(5-(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)-1H-pyrazol-1-yl)piperidin-1-yl)-2-methylpropanoate (150 mg, 0.26 mmol) in Tetrahydrofuran (2.00 mL) at 0° C. was added Lithium Aluminum Hydride (1 mol/L) in THF (0.52 mL, 0.5238 mmol) dropwise. The reaction mixture was slowly allowed to warm up to room temperature and was stirred for 2 hours. LC-MS analysis of the reaction mixture showed no more starting material and the formation of the desired product. The reaction mixture was quenched by the addition of MeOH, filtered and the concentrated. The resulting oil was purified by rHPLC to give 266. 1H NMR (400 MHz, DMSO) δ 8.51 (d, J=8.3 Hz, 1H), 7.98-7.86 (m, 1H), 7.52 (d, J=1.5 Hz, 1H), 7.22 (dd, J=8.3, 1.4 Hz, 1H), 7.09 (s, 1H), 6.39 (t, J=6.8 Hz, 1H), 5.83 (dt, J=13.2, 6.6 Hz, 1H), 4.54 (d, J=15.0 Hz, 4H), 4.36-4.15 (m, 2H), 3.24 (d, J=4.9 Hz, 2H), 3.08 (d, J=8.5 Hz, 1H), 2.93 (t, J=15.9 Hz, 1H), 2.62-2.52 (m, 2H), 2.26 (s, 3H), 2.11 (t, J=10.8 Hz, 1H), 1.92 (s, 2H), 1.73 (d, J=13.1 Hz, 1H), 1.57-1.42 (m, 6H), 0.91 (s, 6H). LCMS: 531.3

Provenance & Evidence