Ethanol → N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874392

반응식

HRID 1874392 반응식
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[CH:19][C:20]4[N:21]([CH:23]=[C:24]([NH:26]C(=O)C(F)(F)F)[N:25]=4)[CH:22]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:33])=[N:3]1.[OH-].[Na+].C(O)C>O>[NH2:26][C:24]1[N:25]=[C:20]2[CH:19]=[CH:18][C:17]([O:16][C:12]3[CH:11]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:33])[CH:5]=4)=[O:8])[CH:15]=[CH:14][CH:13]=3)=[CH:22][N:21]2[CH:23]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 577492691,3-dimethyl-N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1H-pyrazole-5-carboxamide

생성물 1

HCID 57749254N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide수율 79.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

A mixture of 1,3-dimethyl-N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1H-pyrazole-5-carboxamide (328 mg, 0.715 mmol), 1N aqueous sodium hydroxide solution (3 mL) and ethanol (3 mL) was stirred at 40° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80) to give the title compound (205 mg, 79%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate (×3)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80)

출처 및 근거

ORD 기록
ord-e8d24731029c4ab69d016190cc4b6390
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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