1-Hydroxybenzotriazole → HCID 44124031, Verbindung

HRID 600634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600634
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([OH:13])=O)[N:10]=2)[CH:7]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl.[CH3:37][NH:38][O:39][CH3:40]>ClCCl.O.C(N(CC)CC)C>[CH3:40][O:39][N:38]([CH3:37])[C:11]([C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]2[CH:8]=1)=[O:13]

Komponenten

8

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27576146-chloroimidazo[1,2-a]pyridine-2-carboxylic acid

Produkt 1

HCID 44124031HCID 44124031, VerbindungAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 0.784 g of 6-chloroimidazo[1,2-a]pyridine-2-carboxylic acid in 12 mL of dichloromethane are added 1.67 mL of triethylamine, 1.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.08 g of 1-hydroxybenzotriazole. The reaction mixture is stirred for 20 minutes at room temperature. 0.39 g of N,O-dimethylhydroxylamine hydrochloride is added. The reaction mixture is stirred for 4 hours at room temperature. 60 mL of dichloromethane and 30 mL of water are added. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered, evaporated to dryness under reduced pressure, and then purified on a column of silica, eluting with a 95/5 mixture by volume of dichloromethane and methanol. The fractions containing the product are combined and concentrated to dryness under reduced pressure to give 0.6 g of N-methoxy-N-methyl-6-chloroimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Aufarbeitung

  1. stirringThe reaction mixture is stirred for 4 hours at room temperature
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. custompurified on a column of silica
  7. washeluting with a 95/5 mixture by volume of dichloromethane and methanol
  8. additionThe fractions containing the product
  9. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b0b6798e70964e929fc875a3d4a92655
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902219B2

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