Dimethylformamide → N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-cyclopropylacetamide

HRID 1663817

반응식

HRID 1663817 반응식
[CH:1]1([CH2:4][C:5]([NH:7][C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13](I)=[N:12][N:11]3[CH:17]=2)=[O:6])[CH2:3][CH2:2]1.[NH2:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Cl-].[Na+].O.O1CCCC1.C(OCC)(=O)C>[NH2:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:17]=[C:8]([NH:7][C:5](=[O:6])[CH2:4][CH:1]3[CH2:3][CH2:2]3)[N:9]=2)[N:12]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 574410302-cyclopropyl-N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide

생성물 1

HCID 57505552N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-cyclopropylacetamide수율 33%

시약·촉매·용매 2

HCID 21939870Tetrahydrofuran ethyl acetate용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
120 °C

실험 절차

A mixture of 2-cyclopropyl-N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (501 mg, 1.46 mmol), 3-aminophenol (479 mg, 4.39 mmol), potassium carbonate (807 mg, 5.84 mmol) and N,N-dimethylformamide (5 mL) was stirred at 120° C. for 12 hr. Tetrahydrofuran/ethyl acetate and saturated brine were added to the reaction mixture, and insoluble material was filtered off. The filtrate was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80→0/100) to give the title compound (156 mg, 33%) as a pale-yellow powder.

후처리

  1. filtrationwas filtered off
  2. extractionThe filtrate was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80→0/100)

출처 및 근거

ORD 기록
ord-a2c21adf87bd4b14a8dcb517988c9981
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08034812B2

연결된 노트

불러오는 중…