HCID 68312636, compound → HCID 68312824, compound

Participants

Reaction Steps

To a solution of 8-(1-benzyl-3-methylazetidin-3-yloxy)-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (31 mg, 0.064 mmol) in IMS (5 mL) was added Pd(OH)2/C (11 mg) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 16 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (C18, gradient 15-50% MeOH in 0.5% TFA/H2O) and then loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 0.5M NH3/MeOH. Further purifications by column chromatography (Si-PCC, gradient 2-12% 2M NH3/MeOH in DCM) and then (Si-PCC, gradient 3-33% MeOH in DCM) afforded 271 as a colourless gum (5.3 mg, 21%). LCMS (Method K): RT 2.57 min [M+H]+ 395.1. 1H NMR (CD3OD, 400 MHz): δ 8.33 (1H, d, J=9.0 Hz), 7.67 (1H, s), 6.55 (1H, dd, J=9.0, 2.6 Hz), 6.35 (1H, d, J=2.5 Hz), 5.87 (1H, septet, J=6.7 Hz), 4.48 (4H, s), 3.95 (2H, d, J=9.4 Hz), 3.60 (2H, d, J=9.4 Hz), 2.35 (3H, s), 1.70 (3H, s), 1.52 (6H, d, J=6.6 Hz)

Provenance & Evidence