Chloroacetaldehyde → Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

HRID 407076ノート

反応式

HRID 407076 の反応式
[NH2:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.Cl[CH2:19][CH:20]=O>O.C(O)(C)C>[N:1]1[CH:19]=[CH:20][N:7]2[C:2]=1[CH:3]=[C:4]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[N:6]2

参加物

5

反応物 2

HCID 33ChloroacetaldehydeHCID 67980189Methyl 3-(6-aminopyridazin-4-yl)benzoate

生成物 1

HCID 67980108Methyl 3-imidazo[1,2-b]pyridazin-7-ylbenzoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3776Isopropanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 3-(6-aminopyridazin-4-yl)benzoate (0.20 g, 0.87 mmol) and chloroacetaldehyde in water (0.3 mL, 50%) in isopropyl alcohol (3.0 mL) was stirred at 100° C. for 4 h. The solvent was removed and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3, water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%) to afford the desired product (0.18 g). LCMS (M+H)+: m/z=254.1

後処理

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in methylene chloride (0-30%)

出典と根拠

ORDレコード
ord-0232e37fabdc4918b0b3d55ffea65bb1
出典データセット
uspto-grants-2014_06
特許番号
US08754114B2

反応ノート

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