Hydrochloric Acid → HCID 66780320, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-dimethylethyl (2-{[(3-chloro-2-methylphenyl)methyl][5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]amino}-2-oxoethyl)carbamate (150 mg, 0.296 mmol) in Methanol (5 mL) and Water (5.00 mL) was added sodium perborate tetrahydrate (137 mg, 0.889 mmol). The mixture was stirred at 55° C. for 2 hr and then diluted in 100 mL EtOAc. After washed with 100 mL H2O, the organic layer was concentrated and diluted in 10 mL DCM, to which was added 4M HCl in dioxane (0.371 mL, 1.482 mmol). The mixture was stirred at rt for 17 hr. One fourth of the crude material was purified by HPLC and then treated with HCl (6N) to give the titled compound 9 mg (26%). LC/MS (ES) m/z=406.4 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 7.42-7.40 (d, 1H, J=8.0 Hz), 7.18-7.12 (m, 1H), 6.55 (d, 1H, J=8.0 Hz), 5.65 (s, 2H), 4.21 (s, 2H), 3.79-3.76 (m, 4H), 3.68-3.62 (m, 4H), 2.52 (s, 3H).

Provenance & Evidence