1-Phenethylamine → 3-Methyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine

Participants

Reaction Conditions

Reaction Steps

6-Chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine (200 mg, 1.186 mmol; commercially available or prepared according to patent WO2006/039325A2), rac-1-phenylethanamine (575 mg, 4.75 mmol; commercially available from Aldrich) and anhydrous NMP (1 mL) were charged into a microwave tube equipped with a magnetic stirbar (light brown solution). After the vessel was sealed, the mixture was heated at 150° C. for 15 min, followed by an extra 45 min using microwave irradiation. The reaction was then diluted with MeOH/H2O (19:1), filtered, purified by reverse phase chromatography and lyophilized to give the rac-3-methyl-N-(1-phenylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine (Compound 1) as a white solid (42 mg; 14% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.84 (d, J=9.8 Hz, 1H), 7.81 (d, J=7.1 Hz, 1H), 7.42 (d, J=7.8 Hz, 2H), 7.32 (t, J=7.5 Hz, 2H), 7.21 (t, J=7.3 Hz, 1H), 6.80 (d, J=9.8 Hz, 1H), 4.92 (dd, J=7.0, 7.0 Hz, 1H), 2.42 (s, 3H), 1.49 (d, J=6.9 Hz, 3H). LRMS [M+H]+: 254 m/z.

Provenance & Evidence