Acetic Acid → HCID 73051331, compound

Participants

Reaction Steps

0.038 g (0.078 mmol) of methyl 3-(3-((3-((3-(trifluoromethyl)phenyl)ethynyl) imidazo[1,2-a]pyridin-2-yl)methyl)ureido)benzoate were dissolved in 2 ml of a methanol/tetrahydrofurane mixture (1/1, v/v) with magnetic stirring and then 0.931 ml (0.931 mmol) of a (1M) NaOH aqueous solution were added and the mixture was stirred at r.t. for 16 h before being treated with a solution of 0.053 ml (0.931 mmol) of acetic acid in 10 ml of water. The mixture was stirred at r.t. for 30 min. The solid formed was isolated by filtration, washed with 5 ml of water and dried in a vacuum bell jar in order to obtain 0.026 g (yield=70%) of 3-(3-((3-((3-(trifluoromethyl)phenyl)ethynyl)imidazo[1,2-a]pyridin-2-yl)methyl) ureido) benzoic acid as a white solid. LC-MS: m/z=479 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 12.83 (s, 1H), 8.96 (s, 1H), 8.73 (d, J=6.7 Hz, 1H), 8.04 (s, 2H), 7.90 (d, J=7.5 Hz, 1H), 7.69 (dd, J=13.0, 8.4 Hz, 2H), 7.58 (d, J=7.7 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.29 (t, J=7.9 Hz, 1H), 7.13 (t, J=6.8 Hz, 1H), 6.80 (t, J=5.4 Hz, 1H), 4.62 (d, J=5.6 Hz, 2H).

Provenance & Evidence