Dimethylformamide → HCID 58958446, compound

Participants

Reaction Conditions

Reaction Steps

4-Nitrophenyl 5-phenyl-1,3-thiazol-2-ylcarbamate (200.0 mg, 0.59 mmol) along with tert-butyl 1,4-diazepene-1-carboxylate (125.0 ul, 0.64 mmol), diisopropylethylamine (205.5 ul, 2.1 mmol), and dimethylformamide (2.0 ml ) were combined and heated at 60° C. overnight. The reaction was poured into brine (25 ml) containing ammoniumhydroxide (2.0 ml). The mixture was extracted with ethyl acetate (4×25 ml) and the ethylacetate layer back extracted with additional brine/ammonium hydroxide until the yellow color had faded. The ethylacetate layer was dried (MgSO4), and the solvent removed to give tert-butyl 4-{[(5-phenyl-1,3-thiazol-2-yl)amino]carbonyl}-1,4-diazepane-1-carboxylate 24. 1H-NMR (500 MHz, CDCl3): 9.30 (1H, br s), 7.53 (3H, m), 7.37 (2H, t, J=7.81 Hz), 7.28 (1H, t, J=7.08), 3.64 (2H, br s), 3.56 (4H, br s), 3.45 (1H, br s), 3.40 (1H, br s), 1.92 (2H, br s), 1.44 (9H, s). High res. ES MS: Theoretical Mass 403.1798, Measured Mass 403.1801 (C20H26N4O3S+H+)

Provenance & Evidence