HCID 3297125, compound → HCID 66558676, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 9-bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene from Example 6 (200 mg, 0.51 mmol), l′-methyl-[2,4]bipiperidinyl (234 mg, 1.28 mmol), sodium tertbutoxide (148 mg, 1.5 mmol) and Pd(P(tBu)3)2 (13 mg, 0.026 mmol) in dioxane was degassed with a stream of argon and then heated at 100° C. for 1 h in a sealed tube. After cooling to RT, the mixture was diluted with water and extracted with EtOAc (×3). The combined organic phases were concentrated in vacuo and then purified by column chromatography (Si-PCC, gradient 0-10% MeOH in EtOAc, and then with 20% 2M NH3/MeOH in DCM) followed by HPLC purification (Phenomenex Gemini 5 μm C18 on a 25 min gradient 50-95% 0.1% NH4OH in acetonitrile/water) affording 215 (30 mg, 12%). LCMS: RT 2.98 min [M+H]+ 490.2. 1H NMR (CDCl3, 400 MHz): δ 8.27 (1H, d, J=8.98 Hz), 7.51 (1H, s), 6.63 (1H, dd, J=9.25, 2.95 Hz), 6.38 (1H, d J=2.95 Hz), 6.00-5.88 (1H, m), 4.46-4.39 (2H, m), 4.38-4.30 (2H, m), 3.68-3.59 (2H, m), 3.11-3.02 (1H, m), 2.95-2.88 (1H, m), 2.85-2.78 (1H, m), 2.4 (3H, s), 2.25 (3H, s), 1.98-1.60 (11H, m), 1.56 (6H, d, J=7.15 Hz), 1.40-1.19 (2H, m)

Provenance & Evidence