4-Methylmorpholine → HCID 86638103, compound

Participants

Reaction Steps

5-Isopentyl-2-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1,3-thiazole-4-carboxylic acid (330 mg, 0.90 mmol; see Preparation 3(iv) above) was dissolved in DMF (2.5 mL, dry), to which was added NMM (0.1 mL, dry), 2-(4-morpholinyl)ethanamine (117 mg, 0.90 mmol), and HBTU (682 mg, 1.80 mmol) at room temperature with stirring. The stirring was continued at room temperature for 24 h and then the reaction mixture was extracted with sodium hydroxide solution (381 mg, 9.52 mmol in water 10 mL) and ethyl acetate (3×50 mL). The organic layers were collected, dried (MgSO4) and the solvent removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate/methanol containing 1% TEA as eluent (RF=0.15). The sub-title compound was obtained as pale yellow solid (400 mg, 93%).

Provenance & Evidence