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

Participants

Reaction Steps

Following the procedure for 423, 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 and oxazole-2-carbaldehyde were reacted. The crude product was purified by flash chromatography (SiO2, 0-6% 2N NH3/MeOH in DCM) to give an oil. The oil was triturated with ether, the resulting solid filtered off and washed with ether to give 481 as a cream solid (81 mg, 44%). LCMS: RT=3.21 min, [M+H]+=449. 1H NMR δ (ppm) (CDCl3): 8.30 (1H, d, J=8.18 Hz), 7.89 (1H, s), 7.62 (1H, d, J=0.84 Hz), 7.08 (1H, dd, J=8.21, 1.86 Hz), 7.06 (1H, d, J=0.83 Hz), 6.96 (1H, d, J=1.83 Hz), 5.93-5.84 (1H, m), 4.38 (2H, t, J=5.06 Hz), 3.87 (2H, t, J=7.32 Hz), 3.80 (2H, s), 3.78-3.69 (1H, m), 3.41-3.34 (4H, m), 1.60 (6H, d, J=6.63 Hz)

Provenance & Evidence