Acetone → HCID 68312787, compound

Participants

Reaction Steps

To a solution of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-8-((R)-2-piperidin-3-ylazetidin-1-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (64.3 mg, 0.1436 mmol) in a mixture of IMS (5 mL) and acetone (1 mL) was added Pd/C (10%, 15 mg). The mixture was stirred at RT under a balloon of hydrogen for 16 h, then filtered through a celite pad. The filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-15% 2M NH3/MeOH in DCM), then C18, gradient 20-60% MeOH in 0.5% TFA/H2O) and then loaded in MeOH onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH, affording 342 as a colourless foam (28 mg, 40%). LCMS (method K): RT 2.97 min [M+H]+ 490.2. 1H NMR (CD3OD, 400 MHz): δ 8.21 (1H, dd, J=8.7, 2.0 Hz), 7.61 (1H, s), 6.36-6.32 (1H, m), 6.13 (1H, dd, J=5.5, 2.3 Hz), 5.85 (1H, septet, J=6.6 Hz), 4.43 (4H, s), 4.10-3.91 (2H, m), 3.64 (1H, quintet, J=7.9 Hz), 3.06-2.87 (2H, m), 2.75 (1H, septet, J=6.4 Hz), 2.35 (3H, s), 2.33-2.08 (5H, m), 1.85-1.56 (3H, m), 1.51 (6H, d, J=6.6 Hz), 1.98 (0.5H, d, J=10.8 Hz), 1.25-1.11 (1H, m), 1.09 & 1.07 (6H, 2d, J=6.6 Hz)

Provenance & Evidence