Trifluoroacetic acid → HCID 68743041, compound

Participants

Reaction Steps

To a solution of trifluoroacetic acid (2 ml) in dichloromethane (2 ml) was added 4 tert-butyl-4-({[4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)benzoyl]amino}methyl)piperidine-1-carboxylate (68 mg). The mixture was stirred for 1 h, and then concentrated in vacuo to provide 4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)-N-(piperidin-4-ylmethyl)benzamide (67 mg. 99%). Half of this sample was added to potassium carbonate (19 mg) in ethanol. 4-Trifluoromethylbenzyl bromide (17 mg) was added and the mixture was heated to 70° C. for 4 h. The sample was cooled to room temperature, concentrated in vacuo, and was purified via preparative thin-layer chromatography (Rf=0.58 in 1:1 hexanes-ethyl acetate) to provide the title compound (31 mg, 84%). Mass spectrum (ESI) 533.2 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.5 Hz, 2H), 7.94 (d, J=8.4 Hz, 2H), 7.94 (s, 1H), 7.57 (d, J=7.6 Hz, 2H), 7.48 (s, 1H), 7.44 (d, J=7.6 Hz, 2H), 6.23 (t, J=6.4 Hz, 1H), 3.55 (s, 2H), 3.42 (t, J=6.2 Hz, 2H), 2.99 (m, 2H), 2.65 (s, 6H), 2.03 (m, 2H), 1.76, m (2H), 1.42 (m, 3H).

Provenance & Evidence