Aniline → HCID 24771608, Verbindung

HRID 645359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645359
Cl.CN(C)CCCN=C=NCC.O[N:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2N=N1.[CH3:23][C:24]1[C:25]2[N:26]([CH:30]=[C:31]([C:33](O)=[O:34])[N:32]=2)[CH:27]=[CH:28][CH:29]=1.NC1C=CC=CC=1>ClCCl.O.C(N(CC)CC)C>[CH3:23][C:24]1[C:25]2[N:26]([CH:30]=[C:31]([C:33]([NH:14][C:18]3[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:34])[N:32]=2)[CH:27]=[CH:28][CH:29]=1

Komponenten

8

Edukt 4

HCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27598608-methylimidazo[1,2-a]pyridine-2-carboxylic acid

Produkt 1

HCID 24771608HCID 24771608, VerbindungAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

1.67 ml of triethylamine, 1.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.08 g of 1-hydroxybenzotriazole are added to a solution of 0.176 g of 8-methylimidazo[1,2-a]pyridine-2-carboxylic acid in 12 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 20 minutes. 0.090 ml of aniline is added. The reaction mixture is stirred at ambient temperature for 4 hours. 60 ml of dichloromethane and 30 ml of water are added. After separation by settling, the organic phase is dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. After purifying by flash chromatography (silica, eluent dichloromethane/ethyl acetate 98/02 by volume), 0.193 g of 8-methyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide is obtained in the form of a white solid.

Aufarbeitung

  1. stirringThe reaction mixture is stirred at ambient temperature for 4 hours
  2. customAfter separation
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customAfter purifying by flash chromatography (silica, eluent dichloromethane/ethyl acetate 98/02 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-11f3f19d5650425bbfd059c84a85dc6b
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704989B2

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