Sodium Chloride → 2-Tert-butyl-7-(4-fluorophenyl)-N-{(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl}-1,3-benzoxazole-5-carboxamide

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Reaction Conditions

Reaction Steps

To a solution of 2-tert-butyl-7-(4-fluorophenyl)-1,3-benzoxazole-5-carboxylic acid with three equivalents of sodium chloride (30 mg, 74.0 μmol), (1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethanamine dihydrochloride (19.5 mg, 74.0 μmol) and N-methylmorpholine (33.7 μL, 0.307 mmol) in N,N-dimethylformamide (0.409 mL) were added N[2-(dimethylamino)ethyl]-N′-ethylcarbodiimide hydrochloride (20.6 mg, 107 μmol), 1-hydroxy-7-azabenzotriazole (4.2 mg, 31.0 μmol). The mixture was stirred at 40° C. for 1 h. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.05% ammonium hydroxide) gave the title compound (22.6 mg). HRMS [M+1] found=487.1766. 1H NMR (500 MHz, DMSO-d 6): δ 9.15 (2H, s), 8.20 (1H, s), 8.14 (1H, s), 8.02 (2H, t, J=6.70 Hz), 7.45 (2H, t, J=8.65 Hz), 5.33 (1H, m, J=7.09 Hz), 1.63 (3H, d, J=7.07 Hz), 1.47 (9H, s).

Provenance & Evidence