Phenoxyacetyl chloride → HCID 66780191, compound

Participants

Reaction Steps

To a solution of 4-({[2-methyl-3-(trifluoromethyl)phenyl]methyl}amino)-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (100 mg, 0.250 mmol) in Tetrahydrofuran (THF) (1249 μl) at 0° C. was added phenoxyacetyl chloride (69.0 μl, 0.499 mmol). The mixture was stirred at room temperature overnight, then quenched with methanol and concentrated. The residue was purified by reversed-phase HPLC to provide 4-{([2-methyl-3-(trifluoromethyl)phenyl]methyl}-2-(4-morpholinyl)-5-[(phenyloxy)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (14 mg, 11%); LC/MS: MS (ES+) m/e 517 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (s, 3H), 3.48-3.54 (m, 4H), 3.62-3.71 (m, 4H), 5.12 (s, 2H), 5.57 (s, 2H), 6.61 (d, J=7.8 Hz, 2H), 6.85-6.97 (m, 2H), 7.19 (dd, J=8.7, 7.5 Hz, 2H), 7.25-7.33 (m, 1H), 7.60 (d, J=7.8 Hz, 1H).

Provenance & Evidence