1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 67170729, compound

Participants

Reaction Steps

To a stirred solution of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.225 g, 1.00 mmol) in 1,4-dioxane (10 mL) was added (3-aza-bicyclo[3.1.0]hex-6-yl)dibenzyl-amine (0.440 g, 1.200 mmol), 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.5 mL, 3.00 mmol) and tetrabutyl ammonium bromide (0.032 g, 0.10 mmol). The resulting mixture was stirred at reflux for 18 hours. 1,4-Dioxane was removed in vacuo and the obtained crude product was purified by column chromatography to yield the desired product, 6-(6-dibenzylamino-3-azabicyclo[3.1.0]hex-3-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide in 89% yield (0.415 g). 1H NMR (300 MHz, CDCl3) δ 8.00-7.96 (m, 1H), 7.94 (d, J=9.6 Hz, 1H), 7.33-7.21 (m, 10H), 6.56 (d, J=8.5 Hz, 1H), 3.65 (s, 5H), 3.55-3.48 (dd, J=7.0 and 6.3 Hz, 3H), 3.44 (s, 2H), 1.57-1.48 (m, 5H), 0.76-0.67 (m, 1H), 0.46-0.40 (m, 2H), 0.09-0.04 (m, 2H). MS (ES+) m/z 468 (M+1).

Provenance & Evidence