Aniline → HCID 24771608, Verbindung

HRID 1952199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952199
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-dabbcb4af0bb4b46850cd61445a14e3f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404848B2

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