(1S)-2-Chloro-1-methyl-2-oxoethyl acetate → HCID 66780637, 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 (1S)-2-chloro-1-methyl-2-oxoethyl acetate (82 mg, 0.545 mmol). The mixture was stirred at room temperature overnight, then additional (1S)-2-chloro-1-methyl-2-oxoethyl acetate (1 equiv.) was added and stirring was continued at 60° C. for 2 h. The mixture was quenched with methanol and concentrated. The residue was purified by reversed-phase HPLC to provide (1S)-1-[4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]ethyl acetate. (11 mg, 9%); LC/MS: MS (ES+) m/e 463 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (d, J=6.3 Hz, 3H), 1.71 (s, 3H), 2.40 (s, 3H), 3.51-3.54 (m, 4H), 3.67 (m, 4H), 5.48-5.61 (m, 2H), 5.69 (q, J=6.3 Hz, 1H), 6.56 (d, J=7.6 Hz, 1H), 7.16 (m, 1H), 7.38 (d, J=7.8 Hz, 1H).

Provenance & Evidence