Aluminium lithium hydride → HCID 66558924, compound

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution of {1-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]cyclopropyl}-(4-methylpiperazin-1-yl)methanone from Example 50 (90 mg, 0.18 mmol) in THF (5 mL) was added LiAlH4 (1.0M in THF, 0.18 mL) and the mixture was stirred at 0° C. for 2 h. The reaction mixture was quenched by addition of 1N NaOH and then was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by HPLC (Phenomenex Gemini 5 μm C18 on a 25 min gradient 0-60% 0.1% HCO2H in acetonitrile/water) affording 259 (41 mg, 48%). LCMS: RT 2.73 min [M+H]+ 478.1. 1H NMR (DMSO, 400 MHz): δ 8.30 (1H, d, J=8.96 Hz), 8.18 (1H, s), 7.82 (1H, s), 6.82 (1H, dd, J=8.97, 2.49 Hz), 6.63 (1H, d, J=2.47 Hz), 5.89-5.76 (1H, m), 4.48 (4H, s), 2.69 (2H, s), 2.52-2.41 (3H, m), 2.38-2.21 (7H, s), 2.15 (3H, s), 1.45 (6H, d, J=6.60 Hz), 0.96-0.84 (4H, m)

Provenance & Evidence