Tetrahydrofuran → 4-(Imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylic acid

HRID 2046403ノート

反応式

HRID 2046403 の反応式
[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([C:16]([O:18]C)=[O:17])[S:13][C:14]=2[CH3:15])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.C1COCC1.[OH-].[K+]>CO>[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([C:16]([OH:18])=[O:17])[S:13][C:14]=2[CH3:15])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 58046374Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate

生成物 1

HCID 580464044-(Imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
60 °C

実験手順

Methyl 4-(imidazo[1,2-b]pyridazin-3-yl)-5-methylthiophene-2-carboxylate (0.54 g, 1.98 mmol) was dissolved in methanol (9.88 mL) and THF (9.88 mL) and a solution of KOH in methanol was added (1 M, 5.93 mL, 5.93 mmol). The reaction mixture was left to stir overnight at 60° C. The reaction mixture was then cooled to room temperature, concentrated, and acidified with aqueous 1N HCl. The aqueous layer was extracted three times with ethyl acetate, then extracted one time with a 3:1 CHCl3:isopropanol mixture. The combined organics were dried with magnesium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (500 MHz, CD3SOCD3) δ 8.77 (d, 1H); 8.34 (d, 1H); 8.25 (s, 1H); 8.11 (s, 1H); 7.51 (dd, 1H); 2.56 (s, 3H). LRMS (APCI) calc'd for (C12H9N3O2S) [M+H]+, 260.0. found 260.0.

後処理

  1. waitThe reaction mixture was left
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. concentrationconcentrated
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. extractionextracted one time with a 3:1 CHCl3
  6. dry with materialThe combined organics were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a4700d4c094d4b6fbeae3b65e75c56c4
出典データセット
uspto-grants-2013_11
特許番号
US08592425B2

反応ノート

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