Acetone → 8-(1-isopropyl-azetidin-3-yl)-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Participants

Reaction Steps

A suspension of 8-azetidin-3-yl-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene TFA salt 235 (215 mg, 0.45 mmol) in dry DCE (4.5 mL) under argon was treated with acetone (49 μL, 0.67 mmol) followed by sodium triacetoxyborohydride (190 mg, 0.89 mmol). The reaction mixture was stirred at RT for 18 hours. Aqueous saturated sodium bicarbonate solution and DCM were added and the phases were separated. The aqueous phase was extracted with DCM (×2) and the combined organic phase was washed with water followed by brine, dried (Na2SO4) and concentrated in vacuo. The resultant solid was triturated with ether, to give 423 as an off-white solid (115 mg, 63%). LCMS: RT=7.44 min, [M+H]+=410. 1H NMR δ (ppm) (CDCl3): 8.30 (1 H, d, J=8.17 Hz), 7.89 (1 H, s), 7.07 (1 H, dd, J=8.20, 1.83 Hz), 6.96 (1 H, d, J=1.81 Hz), 5.93-5.84 (1 H, m), 4.38 (2 H, t, J=5.05 Hz), 3.79 (2 H, t, J=7.00 Hz), 3.74-3.63 (1 H, m), 3.39 (2 H, t, J=5.06 Hz), 3.12 (2 H, m), 2.38 (1 H, m), 1.60 (6 H, d, J=6.63 Hz), 0.97 (6 H, d, J=6.21 Hz)

Provenance & Evidence