Bis(2-pyridylmethyl)amine → HCID 67404464, Verbindung

HRID 910249

Reaktionsgleichung

Reaktionsgleichung von HRID 910249
[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:20]=[CH:19][N:18]([CH2:21][C:22](O)=[O:23])[N:17]=3)=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:25]1[CH:30]=[C:29]([CH2:31][NH:32][CH2:33][C:34]2[N:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:28]=[CH:27][CH:26]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[N:28]1[CH:27]=[CH:26][CH:25]=[CH:30][C:29]=1[CH2:31][N:32]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][N:39]=1)[C:22](=[O:23])[CH2:21][N:18]1[CH:19]=[CH:20][C:16]([C:13]2[CH:12]=[CH:11][C:10]([C:2]3[N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]4[CH:3]=3)=[CH:15][CH:14]=2)=[N:17]1

Komponenten

8

Edukt 4

HCID 73759Bis(2-pyridylmethyl)amineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67405489HCID 67405489, Verbindung

Produkt 1

HCID 67404464HCID 67404464, VerbindungAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2-[3-(4-Imidazo[1,2-a]pyridin-2-ylphenyl)-1H-1-pyrazolyl]acetic acid (51 mg), 2,2′-dipicolylamine (32 mg), and 1-hydroxybenzotriazole (27 mg) were dissolved in N,N-dimethylformamide (1 mL), and triethylamine (56 μL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) were added to the solution, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with chloroform and then drying over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to flash column chromatography. Fractions eluted by dichloromethane-methanol (20:1) were concentrated under reduced pressure, and the solid was recovered through filtration by use of diethyl ether, to thereby yield the title compound (58 mg).

Aufarbeitung

  1. extractionfollowed by extraction with chloroform
  2. dry with materialdrying over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washFractions eluted by dichloromethane-methanol (20:1)
  5. concentrationwere concentrated under reduced pressure
  6. filtrationthe solid was recovered through filtration by use of diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-f9236efd8d384e90a53a9a1fa0931a3f
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022075B2

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