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

HRID 1874554

Reaktionsgleichung

Reaktionsgleichung von HRID 1874554
[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.Cl[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32]Cl.CN(C)C=O>C(OCC)(=O)C>[CH2:32]1[C:27]2[C:26](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][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

5

Edukt 3

HCID 6228DimethylformamideHCID 119191,2-Bis(chloromethyl)benzeneHCID 57749361N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

Produkt 1

HCID 57749125N-{6-[3-(1,3-dihydro-2H-isoindol-2-yl)phenoxy]imidazo[1,2-a]pyridin-2-yl}cyclopropanecarboxamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of N-[6-(3-aminophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide (19.4 mg, 0.063 mmol), 1,2-bis(chloromethyl)benzene (13.5 mg, 0.077 mmol) and N,N-dimethylformamide (2.0 mL) was stirred at 50° C. for 14 hr. Ethyl acetate was added to the reaction mixture, and 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 (8.8 mg, 34%).

Aufarbeitung

  1. washthe mixture was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2bb8dc8639e54f1286ca2df79970a7c5
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304557B2

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