Diethyl Ether → 3-{3-[4-Methyl-5-(2-morpholin-4-yl-pyridin-4-yl)-thiazol-2-yl]-ureido}-propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 4-Methyl-5-(2-morpholin-4-yl-pyridin-4-yl)-thiazol-2-ylamine hydrobromide (13b) (0.04 g, 0.112 mmol) in DCM (3 ml) is added ethyldiisopropylamine (0.039 ml, 0.224 mmol) to afford a solution. The reaction mixture is then treated with ethyl 3-isocyanatopropionate (0.015 ml, 0.112 mmol) and heated whilst stirring to 60° C. for 5 hours in a sealed reaction vessel. The solution is diluted with DCM and hydrochloric acid (30 ml, 1N HCl) and the layers separated. The aqueous is adjusted to pH 8/9 and extracted with ethyl acetate (3×25 ml). The organics are combined and dried (MgSO4), filtered and concentrated in vacuo to yield a clear oil. Trituration with ether yields the titled compound as a white solid.

Provenance & Evidence