6-Chloroimidazo[2,1-f]pyridazine synthesis

7synthesis methods

Product Name:6-Chloroimidazo[2,1-f]pyridazine
CAS Number:6775-78-6
Molecular formula:C6H4ClN3
Molecular Weight:153.57

107-20-0
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$22.60/5ml

5469-69-2 Synthesis

5469-69-2
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6775-78-6
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$6.00/1g

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-8_pyridazine),7.85 (s, 1H, H-2_Imid),8.22 (d, 1H, J = 9.6 Hz, H-7_pyridazine), 8.34 (s, 1H, H-3_Imid). ¹³CNMR (DMSO-d₆): δ117.99 (CH), 119.40 (CH), 128.21 (CH), 134.99 (CH), 137.67 (C), 146.78(C).HPLC: R_t= 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

5469-69-2 Synthesis

5469-69-2
374 suppliers
$6.00/10g

2032-35-1 Synthesis