Water → HCID 14368349, Verbindung

HRID 1762209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762209
[OH:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1[C:27]([CH2:28]Cl)=[C:26]([NH:30][C:31]([NH2:33])=[O:32])[CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[CH3:11][C:9]1[N:10]=[C:3]2[C:2]([O:1][CH2:28][C:27]3[C:22]([CH3:21])=[CH:23][CH:24]=[CH:25][C:26]=3[NH:30][C:31]([NH2:33])=[O:32])=[CH:7][CH:6]=[CH:5][N:4]2[C:8]=1[CH2:12][C:13]#[CH:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143683478-Hydroxy-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridineHCID 14368348HCID 14368348, Verbindung

Produkt 1

HCID 14368349HCID 14368349, VerbindungAusbeute 12,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 8-hydroxy-2-methyl-3-(2-propynyl) imidazo-[1,2-a]pyridine (0.571 g) and potassium carbonate (0.424 g) in N,N-dimethylformamide (11.5 ml) was stirred at room temperature for 20 minutes under a nitrogen atmosphere and then 6-methyl-2-ureidobenzyl chloride (0.6 g) was added. After being stirred for 2.5 hours. The mixture was poured into water and the resulting precipitates were collected by filtration. The crude product was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (100:1 to 100:4) as eluents to give 2-methyl-8-(6-methyl-2-ureidobenzyloxy)-3-(2-propynyl)imidazo[1,2-a]pyridine (0.13 g).

Aufarbeitung

  1. stirringAfter being stirred for 2.5 hours
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. customThe crude product was purified by column chromatography on silica gel (25 g) with a mixture of chloroform and methanol (100:1 to 100:4) as eluents

Quellen und Nachweise

ORD-Eintrag
ord-84b7024eef6a4200b59c8a635a4093fa
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831041

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