N-(3-Aminopropyl)morpholine → 1-(4-Cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-morpholinopropyl)urea

Participants

Reaction Conditions

Reaction Steps

A mixture of phenyl (4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)carbamate (37 mg, 0.10 mmol) and 3-morpholinopropylamine (0.021 mL, 0.14 mmol) in 0.8 mL dioxane was heated at 80° C. After 2 hours the reaction mixture was evaporated to a yellowish oily film. This material was then chromatographed eluting with EtOAc, then gradient 2% to 6% MeOH in EtOAc to give the title compound as a pale yellow solid (33 mg, 80%). 1H NMR (acetone) δ: 8.38-8.44 (m, 2H), 8.22-8.27 (m, 2H), 6.91 (t, J=5.4 Hz, 1H), 3.59-3.64 (m, 4H), 3.38-3.45 (m, 2H), 2.37-2.45 (m, 6H), 1.77 (quin, J=6.8 Hz, 2H)

Provenance & Evidence