Potassium Carbonate → N-benzyl-4-methyl-2-(2-oxoimidazolidin-1-yl)thiazole-5-carboxamide

To a solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (3.00 g, 12.1 mmol) in tetrahydrofuran (70 mL) was added N,N-diisopropylethylamine (3.13 g, 24.3 mmol), followed by the addition of 2-chloroethyl isocyanate (1.66 g, 15.76 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 2 days. The solvent was removed in vacuo and the residue was washed with water (100 mL) and t-butyl methyl ether (200 mL). The resulting white solid was added to a suspension of potassium carbonate (2.01 g, 14.55 mmol) and tetrabutylammonium iodide (0.16 g, 0.44 mmol) in dioxane (50 mL). The reaction mixture was refluxed for 24 hours. The solvent was removed in vacuo, and the residue was washed with water (200 mL) and ethyl acetate (50 mL). The residue was recrystallized in methanol to afford the title compound as a colorless solid in 60% yield (2.3 g): mp 226-228° C. (methanol); 1H NMR (300 MHZ, DMSO-d6) δ 8.45 (t, J=5.8 Hz, 1H), 7.71 (s, 1H), 7.31-7.16 (m, 5H), 4.33 (d, J=5.8 Hz, 2H), 3.99 (m, 2H), 3.46 (m, 2H), 2.43 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.2, 157.6, 157.1, 151.4, 140.1, 128.6, 127.6, 127.1, 118.1, 44.5, 43.0, 37.7, 17.5; MS (ES+) m/z 317.2 (M+1).

1. customThe resulting reaction mixture
2. customThe solvent was removed in vacuo
3. washthe residue was washed with water (100 mL) and t-butyl methyl ether (200 mL)
4. temperatureThe reaction mixture was refluxed for 24 hours
5. customThe solvent was removed in vacuo
6. washthe residue was washed with water (200 mL) and ethyl acetate (50 mL)
7. customThe residue was recrystallized in methanol

ORD record

ord-d33e801122a54cbea7b0422442801392

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063084B2