Ethanol → (8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

HRID 597858노트

반응식

HRID 597858 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:22][N:23]2C(=O)C3C(=CC=CC=3)C2=O)[C:5]2[N:6]([C:8]([C:12](=[O:21])[C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])=[C:9]([CH3:11])[N:10]=2)[N:7]=1.C(O)C.NN>CC(=O)OCC>[NH2:23][CH2:22][C:4]1[C:5]2[N:6]([C:8]([C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[F:20])=[O:21])=[C:9]([CH3:11])[N:10]=2)[N:7]=[C:2]([Cl:1])[CH:3]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 9321HydrazineHCID 866424872-((6-Chloro-3-(4-chloro-2-fluorobenzoyl)-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)isoindoline-1,3-dione

생성물 1

HCID 86642486(8-(Aminomethyl)-6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)(4-chloro-2-fluorophenyl)methanone

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Combine 2-((6-chloro-3-(4-chloro-2-fluorobenzoyl)-2-methylimidazo[1,2-b]pyridazin-8-yl)methyl)isoindoline-1,3-dione (7.30 g, 15.1 mmol), ethanol (200 mL), and hydrazine (1.45 mL, 3 equiv.) in a round bottom flask and place under nitrogen. Stir for 2 days at RT. Heat for 2 h at 50° C. then concentrate the reaction in vacuo. Dilute with EA. Wash the organics with 1 N HCl (aq) to pull product into the aqueous layer. Make the aqueous layer basic with 1 N NaOH (aq) and extract with EA. Wash the EA layer with aqueous saturated sodium chloride, and dry over anhydrous magnesium sulfate. Filter and concentrate in vacuo to give the title compound crude (1.2 g, 23%) as a light green solid. MS=355.0, 353.0 (M+1).

후처리

  1. temperatureHeat for 2 h at 50° C.
  2. concentrationthen concentrate
  3. customthe reaction in vacuo
  4. washWash the organics with 1 N HCl (aq)
  5. extractionextract with EA
  6. washWash the EA layer with aqueous saturated sodium chloride
  7. dry with materialdry over anhydrous magnesium sulfate
  8. filtrationFilter
  9. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-55f75c1b8e9e451794af892db489d4da
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897600B2

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