Acetoxyacetyl chloride → HCID 66780137, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (200 mg, 0.545 mmol) in Tetrahydrofuran (THF) (2726 μl) at 0° C. was added acetoxyacetyl chloride (117 μl, 1.090 mmol). The mixture was stirred at 50° C. for 3 h, then quenched with methanol and concentrated. The residue was subjected to silica gel chromatography (0-5% methanol/dichloromethane) followed by reversed-phase HPLC purification to provide [4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]methyl acetate. (49 mg, 20%); LC/MS: MS (ES+) m/e 449 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (s, 3H), 2.42 (s, 3H), 3.52 (m, 4H), 3.67 (m, 4H), 5.03 (s, 2H), 5.50 (s, 2H), 6.54 (d, J=7.6 Hz, 1H), 7.17 (m, 1H), 7.39 (d, J=7.8 Hz, 1H).

Provenance & Evidence