2-Methoxyethylamine → N-(2-methoxyethyl)-N'-[4'-methyl-2-(morpholin-4-ylcarbonyl)-4,5'-bi-1,3-thiazol-2'-yl]urea

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Reaction Steps

To N-[4′-methyl-2-(morpholin-4-ylcarbonyl)-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide, prepared in Step III, described above (50 mg; 0.17 mmol; 1 eq.), is added DMF (2 ml) and 2-methoxyethylamine (Fluka)(16 μl; 0.19 mmol; 1.10 eq.). The mixture is stirred 10 min at rt. Solvents are evaporated and the crude product is crystallized in MeOH, affording Compound (36) as a white-off solid (42.1 mg; 60%). 1H NMR (DMSO-d6, 300 MHz) δ 2.41 (s, 3H), 3.30 (m, 5H), 3.39 (m, 2H), 3.68 (m, 6H), 4.33 (m, 2H), 6.67 (m, 1H), 7.91 (s, 1H), 10.41 (br s, 1H). M− (ESI): 410.09; M+ (ESI): 412.12. HPLC (method A), Rt: 2.41 min (purity: 99.7%).

Provenance & Evidence