Phenoxyacetyl chloride → HCID 66780114, compound

Participants

Reaction Steps

To a solution of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (100 mg, 0.273 mmol) in Tetrahydrofuran (THF) (1363 μl) at 0° C. was added phenoxyacetyl chloride (75 μl, 0.545 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-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-[(phenyloxy)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (19 mg, 14%); LC/MS: MS (ES+) m/e 483 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.29 (s, 3H), 3.52 (t, J=4.7 Hz, 4H), 3.67 (t, J=4.7 Hz, 4H), 5.07 (s, 2H), 5.55 (s, 2H), 6.55 (m, 1H), 6.69 (d, J=7.8 Hz, 2H), 6.94 (m, 1H), 7.12 (m, 1H), 7.22 (m, 2H), 7.36 (d, J=7.8 Hz, 1H).

Provenance & Evidence