Tetrahydro-2-furancarbonyl chloride → HCID 66780285, 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 tetrahydro-2-furancarbonyl chloride (73.4 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 μl). The mixture was stirred at room temperature overnight, then additional tetrahydro-2-furancarbonyl chloride (1 equiv.) was added and the mixture was irradiated (uwave) for 15 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-2-furanyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (18 mg, 15%); LC/MS: MS (ES+) m/e 447 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79-1.91 (m, 1H), 1.94-2.05 (m, 2H), 2.35-2.42 (m, 1H), 2.43 (s, 3H), 3.55-3.60 (m, 4H), 3.67 (m, 4H), 3.76 m, 1H), 3.84 (qm, 1H), 4.79 (m, 1H), 5.64 (s, 2H), 6.52 (d, J=7.6 Hz, 1H), 7.14 (m, 1H), 7.37 (d, J=8.1 Hz, 1H).

Provenance & Evidence