Dimethylformamide → N-[6-(3-amino-4-ethylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

HRID 2391291

반응식

HRID 2391291 반응식
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[N:7]=1.[NH2:17][C:18]1[CH:19]=[C:20]([OH:26])[CH:21]=[CH:22][C:23]=1[CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[NH2:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]=1[CH2:24][CH3:25])[O:26][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 183205133-Amino-4-ethylphenolHCID 57386058N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

생성물 1

HCID 57505534N-[6-(3-amino-4-ethylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide수율 70%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (984 mg, 3.0 mmol), 3-amino-4-ethylphenol (617 mg, 4.5 mmol), potassium carbonate (829 mg, 6.0 mmol) and N,N-dimethylformamide (9 mL) was stirred at 150° C. for 24 hr. The reaction mixture was diluted with water and extracted with a mixed solvent of ethyl acetate/tetrahydrofuran (3:1). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100) and recrystallized from a mixed solvent of ethyl acetate/diisopropyl ether to give the title compound (706 mg, yield 70%) as a khaki solid.

후처리

  1. extractionextracted with a mixed solvent of ethyl acetate/tetrahydrofuran (3:1)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  4. customrecrystallized from a mixed solvent of ethyl acetate/diisopropyl ether

출처 및 근거

ORD 기록
ord-4945e478fa9349dc9ce885a454c8b8cf
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273741B2

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