N,N-Dimethylethylenediamine → HCID 90024252, compound

Participants

Reaction Steps

0.896 ml (7.76 mmol) of N,N-dimethylethane-1,2-diamine were solubilized in 8 ml of dichloromethane with magnetic stirring, 0.449 g (0.776 mmol) of 2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methoxy)benzoyl chloride were added and the mixture was stirred at r.t. for 16 h before being concentrated in vacuo. The crude residue was purified by trituration in 20 ml of diisopropyl ether. The solid was isolated by filtration, washed with 10 ml of water and dried in vacuo. 0.178 g (yield=50%) of N-(2-(dimethylamino)ethyl)-2-((3-((4-fluorophenyl)ethynyl)imidazo[1,2-a]-pyridin-2-yl)methoxy)benzamide were obtained as a pale yellow solid. LC-MS: m/z=457 (MH+); UV purity at 254 nm=98%. 1H NMR (300 MHz, DMSO) δ 8.68 (d, J=6.7 Hz, 1H), 8.47 (d, J=4.8 Hz, 1H), 7.91 (dd, J=7.7, 1.5 Hz, 1H), 7.72 (dd, J=8.6, 5.2 Hz, 3H), 7.57-7.39 (m, 3H), 7.32 (t, J=8.9 Hz, 2H), 7.17 (t, J=6.6 Hz, 1H), 7.09 (t, J=7.3 Hz, 1H), 5.51 (s, 2H), 2.5 (1H hidden under the solvent peak), 2.25 (t, J=6.5 Hz, 2H), 1.92 (s, 6H).

Provenance & Evidence