2-(Methylsulfanyl)acetyl chloride → HCID 178518229, 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 1,2-Dimethoxyethane (DME) (1000 μl) was added (methylthio)acetyl chloride (67.9 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 μl). The mixture was stirred at room temperature for 3 h, then irradiated (uwave) at 90° C. for 15 min. After quenching with methanol, the mixture was concentrated and purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-5-[(methylthio)methylthio)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (28 mg, 24%); LC/MS: MS (ES+) m/e 437 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 2.43 (s, 3H), 3.51 (m, 4H), 3.62 (s, 2H), 3.64-3.71 (m, 4H), 5.59 (s, 2H), 6.53 (d, J=7.8 Hz, 1H), 7.15 (m, 1H), 7.38 (d, J=8.01 Hz, 1H).

Provenance & Evidence