Reaktion #68677

Reaktionsgleichung

NaOH

tert-butyl 2-(3-methoxyquinolin-6-yl)acetate

1-(6-chloropyridazin-3-yl)hydrazine

hydrochloric acid

→

desired product

6-((6-chloro-[1,2,4]-triazolo[4,3-b]pyridazin-3-yl)methyl)-3-methoxyquinoline

Lösungsmittel

DCM

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vial was sealed
2. 2
   WaschenThe organic was washed with water
3. 3
   Trocknendried over MgSO4
4. 4
   Sonstigeremoved solvent in vacuo
5. 5
   SonstigeThe crude product was purified
6. 6
   SonstigeA peak at 25 min was collected
7. 7
   SonstigeThe solvent was removed in vacuo

Vorschrift

To a 5 ml CEM microwave tube was added tert-butyl 2-(3-methoxyquinolin-6-yl)acetate (0.05 g, 0.2 mmol), 1-(6-chloropyridazin-3-yl)hydrazine (0.04 g, 0.3 mmol), water (0.5 mL) and hydrochloric acid (0.05 ml, 0.5 mmol). The vial was sealed and first heated at 90° C. for 30 min then placed into CEM microwave for 10 min. at 100° C., with 100 Watts of power via Powermax. The reaction mixture was adjusted the pH to 7 by adding 5 N NaOH—brown ppt. was generated. The brown ppt. was dissolved in DCM. The organic was washed with water, dried over MgSO4, and removed solvent in vacuo. The crude product was purified using SiO2 chromatography (Teledyne Isco RediSep®, P/N 68-2203-026, 12 g SiO2, DCM:EtOAc:MeOH=75%:20%:5%, Flow=30 mL/min). A peak at 25 min was collected. The solvent was removed in vacuo to afford the desired product as light yellowish solid. Wt: 20.0 mg. MS (ESI pos. ion) m/z: 326.53. Calc'd exact mass for C16H12ClN5O: 325.75.

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