(Phenylthio)acetyl chloride → HCID 66780119, 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) was added thiophenoxyacetyl chloride (102 mg, 0.545 mmol). The mixture was stirred at room temperature for 3 h, then irradiated (uwave) at 90° C. for 15 min. The mixture was quenched with methanol, concentrated, and purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-[(phenylthio)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (20 mg, 15%); LC/MS: MS (ES+) m/e 499 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 3.52-3.59 (m, 4H), 3.62-3.73 (m, 4H), 4.18 (s, 2H), 5.59 (s, 2H), 6.52 (d, J=7.8 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.21-7.42 (m, 6H).

Provenance & Evidence