Acetic Acid → HCID 67172438, compound

Participants

Reaction Steps

Ethyl 2-((5-bromopyridin-2-yl)methylamino)acetate (9J1) (41.6 mmol, 11.37 g) was dissolved in dioxane (80 ml) and water (80 ml) and potassium cyanate (62.4 mmol, 5.07 g) added. After 10 min, acetic acid (133 mmol, 8.00 g) was added and the reaction mixture stirred at room temperature under nitrogen overnight. The reaction mixture was quenched with saturated sodium bicarbonate (to pH 8-9) and then extracted with dichloromethane (3×). The organic layers were combined, washed with water, brine and dried using a hydrophobic frit, then concentrated under reduced pressure to give ethyl 2-(1-((5-bromopyridin-2-yl)methyl)ureido)acetate (9J2) 11.08 g (84%) which was used without further purification. 1H NMR (400 MHz, CDCl3) 8.61 (d, 1H) 7.84 (dd 1H) 7.39 (d, 1H) 5.35 (bs, 2H) 4.51 (s, 2H) 4.17 (q, 2H) 4.11 (s, 2H) 1.25 (t, 3H)

Provenance & Evidence