Isopropylamine → 6-Chloro-N-isopropylimidazo[1,2-b]pyridazine-2-carboxamide

HRID 1799588ノート

反応式

HRID 1799588 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13]CC)=O)[N:10]=2)[N:7]=1.C[Al](C)C.[CH:20]([NH2:23])([CH3:22])[CH3:21]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:23][CH:20]([CH3:22])[CH3:21])=[O:13])[N:10]=2)[N:7]=1

参加物

5

反応物 3

HCID 6363IsopropylamineHCID 2779714ethyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylateHCID 16682925Trimethylaluminum

生成物 1

HCID 582166346-Chloro-N-isopropylimidazo[1,2-b]pyridazine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Ethyl 6-chloroimidazo[1,2-b]pyridazine-2-carboxylate (250 mg, 1.11 mmol) was taken up in tetrahydrofuran and cooled to 0° C. Trimethylaluminum (6.6 mL, 13.3 mmol) was added dropwise followed by the addition of isopropylamine (0.4 mL, 2.2 mmol). The cold bath was removed and the reaction was allowed to proceed overnight at room temperature. The reaction was then quenched slowly with methanol, and stirred for 10 minutes. The resulting mixture was filtered, washing the solids with ethyl acetate and water. The filtrate was collected, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organics were concentrated under and purified via flash chromatography (0-15% methanol in dichloromethane) to afford the title compound.

後処理

  1. customThe cold bath was removed
  2. customThe reaction was then quenched slowly with methanol
  3. filtrationThe resulting mixture was filtered
  4. washwashing the solids with ethyl acetate and water
  5. customThe filtrate was collected
  6. customthe phases were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. concentrationThe combined organics were concentrated under and
  9. custompurified via flash chromatography (0-15% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-0bbd9eaa4f9441578311a211e23bd8d8
出典データセット
uspto-grants-2013_01
特許番号
US08344144B2

反応ノート

読み込み中…