Acetone → HCID 66558597, compound

Participants

Reaction Steps

To a solution of 8-(piperidin-3-yloxy)-2-pyridin-2-yl-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 9 (13 mg, 0.036 mmol) in DCM (1 mL) were added acetone (100 uL), AcOH (50 uL) and sodium triacetoxyborohydride (15 mg, 0.072 mmol). The resulting mixture was stirred at RT for 18 h and then diluted with EtOAc. The organic layer was poured into water and the aqueous layer basified with a saturated solution of NaHCO3. The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% 2M NH3/MeOH in DCM) affording 218 as a white solid (11 mg, 76%). LCMS: RT 2.05 min [M+H]+ 405.1. 1H NMR (CDCl3, 400 MHz): δ 8.57-8.51 (2H, m), 8.09 (1H, dt, J=7.95, 1.07 Hz), 7.72 (1H, td, J=7.72, 1.83 Hz), 7.61 (1H, s), 7.16-7.10 (1H, m), 6.75 (1H, dd, J=8.99, 2.58 Hz), 6.57 (1H, d, J=2.55 Hz), 4.50-4.45 (2H, m), 4.43-4.32 (3H, m), 3.13-3.07 (1H, m), 2.85-2.70 (2H, m), 2.26-2.10 (3H, m), 1.86-1.78 (1H, m), 1.48-1.36 (1H, m), 1.26 (1H, s), 1.04 (6H, d, J=6.57 Hz)

Provenance & Evidence