6-Chloroimidazo[2,1-f]pyridazine synthesis
- Product Name:6-Chloroimidazo[2,1-f]pyridazine
- CAS Number:6775-78-6
- Molecular formula:C6H4ClN3
- Molecular Weight:153.57
Yield:6775-78-6 92%
Reaction Conditions:
in water;butan-1-ol at 20; for 18 h;Reflux;
Steps:
6 -Chloroimidazo[1,2-b]pyridazine(1)
Chloroacetaldehyde (9.2 mL, 50% in H2O) wasadded to a solution of 3-amino-6-chloropyridazine (6 g, 46 mmol) in 70 mL n-butanolat room temperature. This mixture was refluxed for 18 h and the then cooled toroom temperature. The resulting precipitate was filtered, washed with butanoland ethyl ether and dissolved in water. NaOH (1N) was added and the extractedwith ethyl acetate and the organic layer was washed with NaHCO3. Theorganic layer was dried over Na2SO4, filtered, andevaporated under reduced pressure to give the compound 1 as a pink amorphous in 92% yield: Mp 116-118 °C; Litt1 115-117.5°C; 1H NMR (CDCl3):δ 7.35 (d, 1H, J = 9.6 Hz, H-8pyridazine),7.85 (s, 1H, H-2Imid),8.22 (d, 1H, J = 9.6 Hz, H-7pyridazine), 8.34 (s, 1H, H-3Imid). 13CNMR (DMSO-d6): δ117.99 (CH), 119.40 (CH), 128.21 (CH), 134.99 (CH), 137.67 (C), 146.78(C).HPLC: Rt= 1.55 min.
References:
Bendjeddou, Lyamin Z.;Loa?c, Nadège;Villiers, Beno?t;Prina, Eric;Sp?th, Gerald F.;Galons, Hervé;Meijer, Laurent;Oumata, Nassima [European Journal of Medicinal Chemistry,2017,vol. 125,p. 696 - 709] Location in patent:supporting information
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