Water → HCID 44160140, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-[4-(5-benzothiazol-2-yl-6-ethoxycarbonylaminopyridin-3-yl)-pyrazol-1-yl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (7.1 mg, 0.013 mmol, 1 eq) and potassium hydroxide (22.2 mg, 0.396 mmol, 30 eq) in 1,2-ethanediol (3 mL), hydrazine hydrate (7 μL, 0.1 mmol, 10 eq) was added and the solution was stirred at reflux (T=200° C.) for 9 h. The reaction mixture was poured into water and extracted with ether. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by prep. TLC [Silicycle, 1000 μm, 20×20 cm plate, developed twice in a 8% 7N NH3(MeOH):CH2Cl2 solvent system.] The desired band was scraped from the plate, the silica gel was completely rinsed of all product, and the filtrate was concentrated in vacuo, giving the title compound as a yellow solid. MS (ES+): m/z=403.17 (40) [MH+]. HPLC: tR=2.37 min (ZQ3, polar—5 min).

Provenance & Evidence