Water → Ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzo[d]thiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-(6-bromopyridazin-4-yl)-7-(pyridin-2-yl)benzothiazol-2-yl)-3-ethylurea (Intermediate 10) (0.090 g, 0.19 mmol) in DMF (2 mL) was added Et3N (0.08 mL, 0.57 mmol) followed by the addition of ethyl 4-methylpiperidine-4-carboxylate hydrochloride (0.06 g, 0.29 mmol) and the mixture heated to 90° C. for 20 h then cooled to rt, water added and extracted with EtOAc (3×75 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 3% MeOH: DCM to obtain the desired product as yellow solid (0.05 g, 47%). MS: 546.40 [M+H]+.

Provenance & Evidence