Water → HCID 22000389, compound

Participants

Reaction Steps

To a stirred solution of N2-[(4-aminocyclohexyl)methyl]-4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2-amine (0.600 g, 1.49 mmol) in anhydrous pyridine (3 ml) and diisopropylethylamine (3 ml) was added propionyl chloride (0.155 ml, 1.78 mmol) dropwise. The solution was stirred for 1 hour at room temperature and poured into water (60 ml). The solution was extracted with EtOAc and the solvent removed in vacuo to yield a viscous golden oil. The oil was chromatographed on silica-gel eluting with 70% EtOAc/30% hexane to yield 74% (425 mg) of an orange solid: m.p. 70-73° C. 1H-NMR (CDCl3) δ 1.10 (6H, m), 1.60 (1H, broad), 1.83 (3H, m), 2.00 (3H, m), 2.17 (2H, q, J=7.6 Hz), 3.13 (4H, q, J=5.1 Hz), 3.73 (1H, broad), 4.32 (2H, t, J=5.3 Hz), 5.32 (1H, broad), 7.00 (1H, dd, J=6.4 Hz). ESIMS m/z=386 (MH+).

Provenance & Evidence