Phthalaldehyde → N-{6-[3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide

HRID 1874555

반응식

HRID 1874555 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1.[C:24]1([CH:32]=O)[C:25]([CH:30]=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1>C(O)(=O)C>[O:31]=[C:30]1[C:25]2[C:24](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:32][N:1]1[C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[CH:11]=1

참가 물질

4

반응물 2

HCID 4807PhthalaldehydeHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

생성물 1

HCID 57749302N-{6-[3-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamide수율 18%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (19.7 mg, 0.064 mmol), benzene-1,2-dicarbaldehyde (10.7 mg, 0.080 mmol) and acetic acid (4.0 mL) was stirred at 100° C. for 13 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was concentrated, and the residue was purified by preparative HPLC to give the title compound (4.8 mg, 18%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-2949d892ffaf4626bd4349bd0ad24ca1
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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