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

HRID 1874555

Reaktionsgleichung

Reaktionsgleichung von HRID 1874555
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2949d892ffaf4626bd4349bd0ad24ca1
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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