1-Ethylpiperazine → 10-[1-(4-Ethylpiperazin-1-yl)ethyl]-9-fluoro-2-(2-isopropyl-5-methyl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine

Participants

Reaction Steps

A solution of 9-(1-bromoethyl)-8-fluoro-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (85 mg, 0.20 mmol), N-ethylpiperazine (27 μL, 0.22 mmol) and DIPEA (54 μL, 0.30 mmol) in dioxane (2 mL) was stirred at RT for 24 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (Si-PPC, gradient 0-10% 2 M NH3/MeOH in DCM) to give 374 (61 mg, 0.13 mmol, 65% over 2 steps) as a white solid. LCMS (Method K): RT 2.74 min [M+H]+ 468.2. 1H NMR (CD3OD, 400 MHz): δ 8.55 (1H, d, J=8.2 Hz), 7.68 (1H, s), 6.76 (1H, d, J=11.1 Hz), 5.83 (1H, sept., J=6.7 Hz), 4.48 (4H, br s), 3.84 (1H, q, J=6.8 Hz), 2.50 (8H, br s), 2.38 (2H, q, J=7.4 Hz), 2.33 (3H, s), 1.53 (3H, d, J=6.7 Hz), 1.52 (3H, d, J=6.7 Hz), 1.40 (3H, d, J=6.8 Hz), 1.03 (3H, t, J=7.4 Hz)

Provenance & Evidence