TETRAHYDROPYRAN-2-CARBONYL CHLORIDE → HCID 66780356, compound

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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 ul) was added tetrahydro-2H-pyran-2-carbonyl chloride (81 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 ul). The mixture was stirred at room temperature for 3 h, then irradiated (uwave) for 20 min at 90° C. 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-(tetrahydro-2H-pyran-2-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (17 mg, 14%); LC/MS: MS (ES*) m/e 461 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (br. s., 3H), 1.62-1.72 (m, 1H), 1.78-1.98 (m, 2H), 2.45 (s, 3H), 3.45-3.57 (m, 5H), 3.66 (t, J=4.8 Hz, 4H), 3.81 (d, J=11.6 Hz, 1H), 4.28 (m, 1H), 5.51-5.66 (m, 2H), 6.49 (d, J=7.8 Hz, 1H), 7.13 (m, 1H), 7.36 (d, J=7.8 Hz, 1H).

Provenance & Evidence